BR112020008084B1 - PHENYL ETHERS, HERBICIDAL COMPOSITION, PROCESS FOR PREPARING ACTIVE COMPOSITIONS, METHOD FOR CONTROLLING UNWANTED VEGETATION AND USE OF PHENYL ETHERS - Google Patents

Abstract

The present invention relates to phenyl ethers of formula (I): or their salts or derivatives acceptable for agricultural use, in which the variables are defined in accordance with the specification, processes and intermediates for preparing the phenyl ethers of formula (I ), compositions comprising them and their use as herbicides, i.e. to control weeds, and also a method of controlling unwanted vegetation comprising maintaining a herbicide-effective amount of at least one phenyl ether of formula (I) for action on plants, their seeds and/or their habitat.

Description

[001] The present invention relates to phenyl ethers of the general formula (I) defined below and their use as herbicides. Furthermore, the present invention relates to plant protection compositions and a method of controlling unwanted vegetation.

[002] WO 02/098227, EP 1,106,607 and EP 1,122,244 describe structurally similar compounds, while the compounds according to the present invention are characterized by a different heterocycle Y.

[003] The herbicidal properties of these known compounds in relation to weeds, however, are not always completely satisfactory.

[004] It is, therefore, the object of the present invention to provide phenyl ethers of formula (I) that have improved herbicidal action. Phenyl ethers of formula (I) that have high herbicidal activity, particularly even at low application rates, and that are sufficiently compatible with producing plants for commercial use, must be particularly provided.

[005] These and other objects are achieved by the phenyl ethers of formula (I), defined below, and their agriculturally appropriate salts.

[006] Consequently, the present invention provides phenyl ethers of formula (I): wherein the substituents have the following meanings: R1 is H or halogen; - R2 is H, halogen, CN, NO2, NH2, CF3 or C(=S)NH2; - R3 is H, halogen, CN, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, (C1-C3 alkyl)amino, dialkyl(C1-C3)amino, C1-C3 alkoxy C1-C3 alkyl or C1-C3 alkoxycarbonyl; - R4 is H, halogen, C1-C3 alkyl or C1-C3 alkoxy; - R5 is OR6, SR6, NR7R8, NR6OR6, NR6S(O)2R7 or NR6S(O)2NR7R8; where - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1 alkoxy -C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, haloalkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1C6 alkyl, haloalkenyloxy C3-C6 alkyl, C3 alkenyloxy -C6 alkoxy, C1-C6 alkyl, C1-C6 alkylthio, C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 haloalkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, amino, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1-C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1-C6 aminocarbonylalkyl, (C1-C6 alkyl)aminocarbonylC1- C6 or di(C1-C6 alkyl)aminocarbonylC1-C6alkyl; -N=CR9R10, where R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 heterocyclyl, C3-C6 heterocyclyl, C1C6 alkyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R13 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of: -N(R9)-, -N=N-, -C(=O)-, - O- and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; and wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; - R7 and R8, independently of each other, are R6 or together they form a carbocycle with 3 to 7 members; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R9)-, -N=N-, -C(=O)-, -O - and -S-; and - m that the carbocycle is optionally substituted by one to four substituents selected from R11; - n is 1 to 3; - Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; - W is O or S; - X is O or S; - Y is a heterocycle selected from the group consisting of Y1 to Y73: where - A1, A2 and A3 are oxygen or sulfur; - A4 is oxygen, sulfur, SO or SO2; - R12, R13, R14, R15, R16, R17 and R18 are hydrogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1C6 alkoxy, C1-C6 haloalkoxy, C2-alkenyl C6, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkoxysulfonyl, C1-C6 alkylsulfonyloxy, amino, alkylamino C1-C6 or di(C1-C6 alkyl)amino; or - R12 and R13, together with the atoms to which they are bonded, form a cycle with three to six members, which is saturated, partially unsaturated or aromatic, which may comprise, in addition to carbon atoms, one to four nitrogen atoms , one or two oxygen atoms, one or two sulfur atoms, one to three nitrogen atoms and one oxygen atom, one to three nitrogen atoms and one sulfur atom, or one sulfur atom and one oxygen atom, which , for the most part, can be totally or partially halogenated and/or substituted by one to three radicals from the group consisting of C1-C6 alkyl and C1-C6 alkoxy; - R19, R20, R21, R22, R23 and R24 are hydrogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, haloalkoxy C1-C6, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 phenylalkyl, amino, C1-C6 alkylamino or di(C1-C6 alkyl)amino; or - R21 and R22, together with the atoms to which they are bonded, form a three- to six-membered cycle, which is saturated, partially unsaturated or aromatic, which may comprise, in addition to carbon atoms, one to four nitrogen atoms , one or two oxygen atoms, one or two sulfur atoms, one to three nitrogen atoms and one oxygen atom, one to three nitrogen atoms and one sulfur atom, or one sulfur atom and one oxygen atom, which , for the most part, can be totally or partially halogenated and/or substituted by one to three radicals from the group consisting of C1-C6 alkyl and C1-C6 alkoxy; - R25 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkoxy, amino, C1-C6 alkylamino or di(C1-C6 alkyl)amino; - R26 and R27 are hydrogen, halogen or C1-C6 alkyl; - R28, R29 and R30 are hydrogen, halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1- haloalkylthio C6, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl or C3-C6 alkynyloxy; and - R31 is hydrogen, NH2, C1-C6 alkyl or C3-C6 alkynyl; - R32, R33 and R34 are hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1 haloalkoxy -C6, C1C6 alkylthio, C1-C6 haloalkylthio, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkoxycarbonyl, C2-C6 alkenylthio, C3-C6 alkynylthio , C1-C6 alkylamino, di(C1-C6 alkyl)amino or C3-C7 cycloalkyl C1-C3 alkyl; - R35 and R36 are hydrogen, cyano, hydroxyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C6 alkynyl , C1-C6 alkoxycarbonyl, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, C3-C7 cycloalkyl C1-C3 alkyl, phenyl or C1-C6 phenylalkyl; - R37 is halogen or C1-C6 alkyl; and - Z is phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl; each optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1C6 alkoxy or C1-C6 haloalkoxy; including its agriculturally acceptable salts or derivatives, provided that the compounds of formula (I) contain a carboxyl group.

[007] The present invention also provides agrochemical compositions comprising at least one phenyl ether of formula (I) and customary auxiliaries for the formulation of plant protection agents.

[008] The present invention also provides herbicidal compositions comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B (component B) and safety agents C (component W).

[009] The present invention also provides for the use of phenyl ethers of formula (I) as herbicides, that is, for the control of weeds.

[010] The present invention further provides a method of controlling unwanted vegetation, in which a herbicide-effective amount of at least one phenyl ether of formula (I) is allowed to act on plants, their seeds and/or their habitat. Application can be carried out before, during and/or after, preferably during and/or after the emergence of undesirable plants.

[011] Furthermore, the present invention relates to processes and intermediates for preparing phenyl ethers of formula (I).

[012] Additional embodiments of the present invention are evident from the claims, the specification and the examples. It should be understood that the characteristics mentioned above and those yet to be illustrated below the object of the present invention can be applied not only to the combination provided in each specific case, but also to other combinations, without abandoning the scope of the present invention.

[013] As used herein, the terms “control” and “combat” are synonymous.

[014] As used herein, the expressions “undesirable vegetation” and “weed plants” are synonymous.

[015] If the phenyl ethers of formula (I), the herbicidal compounds B and/or the safety agents C described herein are capable of forming geometric isomers, such as E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the present invention.

[016] If the phenyl ethers of formula (I), the herbicidal compounds B and/or the safety agents C described herein contain one or more chirality centers and, consequently, are present as enantiomers or diastereomers, it is possible to use both , the pure enantiomers and diastereomers and mixtures thereof, in the compositions according to the present invention.

[017] If the phenyl ethers of formula (I), the herbicidal compounds B and/or the safety agents C described herein contain ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Generally suitable are salts of these cations and acid addition salts of these acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

[018] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably manganese, copper, zinc and iron, additional ammonium and substituted ammonium, in which one to four hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 hydroxyalkoxy C1-C4 alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyethyl- 1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl )ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), additionally phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium and sulfoxonium ions, preferably tri( C1-C4 alkyl)sulfoxonium and, finally, salts of polybasic amines, such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[019] Anions of useful acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methylsulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate.

[020] Phenyl ethers of formula (I), herbicidal compounds B and/or safety agents C described herein that contain a carboxyl group can be employed in the form of an acid, in the form of an agriculturally appropriate salt as mentioned above or in the form of agriculturally acceptable derivative, for example amides, such as mono- and C1-C6 dialkyl amides or arylamides, as esters, for example as allyl esters, propargyl esters, C1-C10 alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2- yl)methyl) esters and also as thioesters, such as C1-C10 alkylthio esters. Preferred C1-C6 mono- and dialkyl amides are methyl and dimethyl amides. Preferred arylamides are, for example, anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or iso-octyl (2- ethylhexyl) esters. Preferred C1-C4 alkoxy C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxy ethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched C1-C10 alkylthio ester is ethylthio ester.

[021] The organic portions mentioned in the definition of variables R3 to R37 and Ra to Re are - like the term halogen - collective terms for individual indications of members of individual groups. The term halogen indicates, in each case, fluorine, chlorine, bromine or iodine. All hydrocarbon chains, that is, all alkyl, alkenyl, alkynyl and alkoxy chains, can be straight-chain or branched, where the prefix Cn-Cm indicates, in each case, the possible number of carbon atoms in the group .

[022] Examples of these meanings are: - C1-C3 alkyl and also the C1-C3 alkyl moieties of di(C1-C3 alkyl)amino, C1-C3 alkoxy C1-C3 alkyl: for example, CH3, C2H5, n-propyl and CH(CH3)2; - C1-C4 alkyl and also the C1-C4 alkyl moieties of C1-C4 phenylalkyl: e.g. CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH (CH3)2 and C(CH3)3; - C1-C6 alkyl and also the C1-C6 alkyl moieties of C1-C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1 alkyl -C6, C1-C6 haloalkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkyl, C3-C6 haloalkenyloxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1- C6, C1-C6 alkylsulfinyl C1C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 haloalkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6, C3-C6 alkynyloxycarbonyl, C1-C6 alkyl, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1- aminocarbonylalkyl C6, (C1-C6 alkyl)aminocarbonylC1-C6 alkyl, di(C1-C6 alkyl)aminocarbonylC1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl, heterocyclyl C3-C6 alkyl: C1-C4 alkyl as mentioned above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl; - C1-C3 haloalkyl: C1-C3 alkyl, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl )-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl or 1-(bromomethyl)-2-bromoethyl; - C1-C4 haloalkyl: C1-C4 alkyl, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl )-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2-tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl; - C1-C6 haloalkyl: C1-C4 haloalkyl as mentioned above and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6 -bromohexyl, 6-iodohexyl and dodecafluorohexyl; - C3-C6 alkenyl and also the C3-C6 alkenyl moieties of C3-C6 alkenyloxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkoxy C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl: e.g. propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl- 1-propenyl, 1-methyl-2-propenyl, 2-methyl- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2- propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2- methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl- 3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1- dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3- dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1- ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; - C3-C6 haloalkenyl, as well as the C3-C6 haloalkenyl moieties of C3-C6 haloalkenyloxy C1-C6 alkyl: C3-C6 alkenyl radical as mentioned above, which is fully or partially replaced by fluorine, chlorine, bromine and/or iodine, such as 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en- 1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop- 2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1- yl or 2,3-dibromobut-2-en-1-yl; - C3-C6 alkynyl, as well as the C3-C6 alkynyl moieties of C3-C6 alkynyloxycarbonyl C1-C6 alkyl: e.g. 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl -2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexinyl, 1-methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl -1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3 -butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; - C3-C6 haloalkynyl: C3-C6 alkynyl radical, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as 1,1-difluoroprop-2-yn-1-yl, 3 -chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut -2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent -4-yn-1-yl, 6-fluoro-hex-4-yn-1-yl or 6-iodo-hex-5-yn-1-yl; - C1-C3 alkoxy and also the C1-C3 alkoxy moieties of C1-C3 alkoxy C1-C3 alkyl and C1-C3 alkoxycarbonyl: for example, methoxy, ethoxy and propoxy; - C1-C4 alkoxy, as well as the C1-C4 alkoxy moieties of C1-C4 alkoxycarbonyl: for example, methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy; - C1-C6 alkoxy, as well as the C1-C6 alkoxy moieties of C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, alkenyloxy C3-C6 alkoxy C1-C6 alkyl C1-C6 alkoxy and C1-C6 alkoxycarbonyl C1-C6 alkyl: C1-C4 alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy; - C1-C3 haloalkoxy: C1-C3 alkoxy radical as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3- difluoropropoxy, 2,3- dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3- pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1- (chloromethyl)-2-chloroethoxy and 1-(bromomethyl)-2-bromoethoxy; - C1-C4 haloalkoxy: C1-C4 alkoxy radical as mentioned above, which is fully or partially replaced by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3- difluoropropoxy, 2,3- dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3- pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1- (chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; - C1-C6 haloalkoxy and also the C1-C6 haloalkoxy moieties of C1-C6 haloalkoxy C1-C6 alkyl, C1-C6 haloalkoxycarbonyl C1-C6 alkyl: C1-C4 haloalkoxy as mentioned above, as well as, for example, 5- fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy; - C1-C3 alkylthio: for example, methylthio, ethylthio, propylthio and 1-methylethylthio; - C1-C4 alkylthio: for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio; - C1-C6 alkylthio, as well as the C1-C6 alkylthio moieties of C1-C6 alkylthio C1-C6 alkyl: C1-C4 alkylthio, as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3 -methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2 - trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; - C1-C6 alkylsulfinyl (C1-C6 alkyl-S(=O)-), as well as the C1-C6 alkylsulfinyl moieties of C1-C6 alkylsulfinyl C1-C6 alkyl: for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1- methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2- dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2- dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3- methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2- dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3- dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl; - C1-C6 alkylsulfonyl (C1-C6 alkyl S(O)2-), as well as the C1-C6 alkylsulfonyl moieties of C1-C6 alkylsulfonyl C1-C6 alkyl; for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl , 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl , 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl , 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl; - (C1-C3 alkyl)amino: for example, methylamino, ethylamino, propylamino and 1-methylethylamino; - (C1-C4 alkyl)amino: for example, methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino; - (C1-C6 alkyl)amino: (C1-C4 alkylamino) as mentioned above and also, for example, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2- dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl- 2-methylpropylamino; - di(C1-C6 alkyl)amino: di(C1-C4 alkyl)amino as mentioned above, as well as, for example, N-methyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N -methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl )amino, N-methyl-N-hexylamino, N-methyl-N-(1,1-dimethylpropyl)amino, N-methyl-N-(1,2-dimethylpropyl)amino, N-methyl-N-(1- methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-( 1,1-dimethylbutyl)amino, N-methyl-N-(1,2-dimethylbutyl)amino, N-methyl-N-(1,3-dimethylbutyl)amino, N-methyl-N-(2,2-dimethyl) - butyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dimethylbutyl)amino, N-methyl-N-(1-ethylbutyl)amino, N- methyl-N-(2-ethylbutyl)amino, N-methyl-N-(1,1,2-trimethylpropyl)amino, N-methyl-N-(1,2,2-trimethylpropyl)amino, N-methyl-N -(1-ethyl-1-methylpropyl)amino, N-methyl-N-(1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentylamino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1- ethylpropyl)amino, N-ethyl-N-hexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino, N-ethyl-N-(1,2-dimethylpropyl)amino, N-ethyl-N-(1 -methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl)amino, N-ethyl-N-(4-methylpentyl)amino, N-ethyl-N- (1,1-dimethylbutyl)amino, N-ethyl-N-(1,2-dimethylbutyl)amino, N-ethyl-N-(1,3-dimethylbutyl)amino, N-ethyl-N-(2,2- dimethylbutyl)amino, N-ethyl-N-(2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethylbutyl)amino, N-ethyl -N-(2-ethylbutyl)amino, N-ethyl-N-(1,1,2-trimethylpropyl)amino, N-ethyl-N-(1,2,2-trimethylpropyl)amino, N-ethyl-N- (1-ethyl-1-methylpropyl)amino, N-ethyl-N-(1-ethyl-2-methylpropyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, N,N-dipentyl- amino, N-propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino or N,N-dihexylamino; - C3-C6 cycloalkyl and also the cycloalkyl moieties of C3-C6 cycloalkyl C1-C6 alkyl: monocyclic saturated hydrocarbons containing three to six ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; - C3-C6 heterocyclyl, as well as the heterocyclyl moieties of C3-C6 heterocyclyl C1-C6 alkyl: aliphatic heterocycle that contains 3 to 6 ring members that, in addition to carbon atoms, contains 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen atom or a sulfur atom, such as three- or four-membered heterocycles, such as 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1 -azetidinyl, 2-azetidinyl, 1-azetinyl and 2-azetinyl; saturated five-membered heterocycles such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 2-isothiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2- thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4- imidazolidinyl, 3-oxazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5- yl, 3-thiazolidinyl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,2,4-oxadiazolidin- 2-yl, 1,2,4-oxadiazolidin-4-yl, 1,3,4-oxadiazolidin-2-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazolidin-4- yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl and 1,3,4-triazolidin-2-yl; saturated six-membered heterocycles such as 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 1,4-dioxanyl, 1,3-dithian-5-yl, 1,3-dithianyl, 1,3-oxathian-5-yl, 1,4- oxathianyl, 2-tetrahydropyranyl, 3-tetrahydopyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetra- hydrothiopyranyl, 4-tetrahydrothiopyranyl, 1-hexahydropyridazinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 1-piperazinyl, 2- piperazinyl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-1-yl, 1,2,4- hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-1-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl, 1-morpholinyl, 2-morpholinyl and 3-morpholinyl; - 5- or 6-membered heteroaryl: aromatic heteroaryl that contains 5 or 6 ring members that, in addition to carbon atoms, contains 1 to 4 nitrogen atoms, 1 to 3 nitrogen atoms and an oxygen or sulfur atom or an atom of oxygen or sulfur, such as five-membered aromatic rings such as furyl (e.g., 2-furyl and 3-furyl), thienyl (e.g., 2-thienyl and 3-thienyl), pyrrolyl (e.g., pyrrole-2 -yl and pyrrole-3-yl), pyrazolyl (e.g. pyrazol-3-yl and pyrazol-4-yl), isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl and isoxazol-5-yl ), isothiazolyl (e.g. isothiazol-3-yl, isothiazol-4-yl and isothiazol-5-yl), imidazolyl (e.g. imidazol-2-yl and imidazol-4-yl), oxazolyl (e.g. oxazol -2-yl, oxazol-4-yl and oxazol-5-yl), thiazolyl (e.g. thiazol-2-yl, thiazol-4-yl and thiazol-5-yl), oxadiazolyl (e.g. 1,2 ,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4 -oxadiazol-2-yl), thiadiazolyl (e.g., 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl and 1,3,4-thiadiazolyl-2-yl), triazolyl (e.g. 1,2,3-triazol-4-yl and 1,2,4-triazol-3 -ila); 1-tetrazolyl; six-membered aromatic rings such as pyridyl (e.g. pyridin-2-yl, pyridin-3-yl and pyridin-4-yl), pyrazinyl (e.g. pyridazin-3-yl and pyridazin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), pyrazin-2-yl, and triazinyl (e.g., 1,3,5-triazin-2-yl, 1,2 ,4-triazin-3-yl, 1,2,4-triazin-5-yl and 1,2,4-triazin-6-yl); - carbocycle with 3 to 7 members: monocyclic aromatic cycle with three to seven members, saturated, partially unsaturated or aromatic, which contains three to seven ring members and comprises, in addition to carbon atoms, optionally one or two selected ring members from the group consisting of -N(R12)-, -N=N-, -C(=O)-, -O- and -S-.

[023] The preferred embodiments of the present invention mentioned below need to be understood as being preferred independently or in combination with each other.

[024] According to a preferred embodiment of the present invention, preference is also given to the phenyl ethers of formula (I), in which the variables, independently or in combination with each other, have the following meanings.

[025] Phenyl ethers of formula (I) are preferred, where: - R1 is H, F or Cl; with specific preference, H or F; of special preference, H; also preferably specifically, H or Cl; preferably special, Cl; also of specific preference, F or Cl; and with special preference, F.

[026] Phenyl ethers of formula (I) are also preferred, in which: - R2 is halogen or CN; preferably, F, Cl, Br or CN; preferably specifically, F, Cl or CN; preferably special, Cl or CN; more preferably, Cl; also more preferably, CN; also with special preference, F or Cl; and most preferably, F.

[027] Phenyl ethers of formula (I) are also preferred, wherein: - R3 is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; specifically preferably, H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy; especially preferably, H, C1-C3 alkyl or C1-C3 alkoxy; and more preferably, H, CH3 or OCH3.

[028] Phenyl ethers of formula (I) are also preferred, where: - R4 is H, halogen or C1-C3 alkyl; preferably specifically, H, F or CH3; and with special preference, H.

[029] Phenyl ethers of formula (I) are also preferred, wherein: - R5 is OR6, SR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; preferably specifically, OR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; especially preferably, OR6, NR6S(O)2R7 or NR6S(O)2NR7R8; especially preferably OR6 or NR6S(O)2R7.

[030] Phenyl ethers of formula (I) are also preferred, in which: - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3- haloalkynyl C6, C1C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 haloalkoxy C1-C6 alkyl, C3 alkenyloxy -C6 alkyl C1C6, haloalkenyloxy C3-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkoxy C1C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1- ( C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1-C6 aminoalkyl, di(C1-C6 alkyl)C1-aminoalkyl C6, C1-C6 aminocarbonylalkyl, (C1-C6 alkyl)C1-C6 aminocarbonylalkyl or di(C1-C6 alkyl)aminocarbonylC1-C6 alkyl; - N=CR9R10; wherein R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 heterocyclyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R11 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R9)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; preferably, it is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1C6 alkyl or C3-C6 cycloalkyl C1-C6 alkyl; specifically preferably, it is hydrogen, C1-C6 alkyl, C3C6 alkenyl, C3-C6 alkynyl or C1-C6 haloalkyl; especially preferably, it is hydrogen, C1-C6 alkyl or C3C6 alkynyl; and more preferably, it is hydrogen, CH3, C2H5 or CH2C=CH.

[031] Phenyl ethers of formula (I) are also preferred, where: - R7 is H or C1-C6 alkyl; most preferably, H; and also more preferably, C1-C6 alkyl.

[032] Phenyl ethers of formula (I) are also preferred, where: - R8 is H or C1-C6 alkyl; most preferably, H; and also more preferably, C1-C6 alkyl.

[033] Phenyl ethers of formula (I) are also preferred, where: - R9 is phenyl or C1-C4 alkyl; preferably specifically, phenyl or CH3; also specifically preferably, phenyl; and also specifically preferably, C1-C4 alkyl.

[034] Phenyl ethers of formula (I) are also preferred, where: - R10 is phenyl or C1-C4 alkyl; preferably specifically, phenyl or CH3; also specifically preferably, phenyl; and also specifically preferably, C1-C4 alkyl.

[035] Phenyl ethers of formula (I) are also preferred, in which: - R11 is halogen or C1-C6 alkyl; preferably specifically, F, Cl or CH3; also of specific preference, halogen; preferably special, F or Cl; also specifically preferably, C1-C6 alkyl; and especially preferably, CH3.

[036] Phenyl ethers of formula (I) are also preferred, where: n is 1 or 2; of specific preference, 2; and also of specific preference, 1.

[037] Phenyl ethers of formula (I) are also preferred, where: - Q is O or S; of specific preference, O.

[038] Phenyl ethers of formula (I) are also preferred, where: - W is O; and also preferably, S.

[039] Phenyl ethers of formula (I) are also preferred, where: - X is O; and also preferably, S.

[040] According to a preferred embodiment of the present invention, preference is also given to the phenyl ethers of formula (I), in which the variables, independently or in combination with each other, have the following meanings: - Y is preferably Y2, Y13 , Y20, Y31, Y37, Y38, Y39, Y42, Y48, Y55, Y65, Y66, Y67 or Y68; preferably specifically, Y2, Y20, Y26, Y31, Y37, Y38, Y42, Y48, Y55, Y65, Y66, Y67 or Y68; especially preferably Y2, Y20, Y26, Y37, Y42, Y55, Y65, Y66 or Y67; and more preferably, Y2, Y20, Y55, Y65 or Y67; - A1 and A2 are preferably oxygen; and also preferably, sulfur; - A3 is preferably oxygen; and also more preferably, sulfur; - A4 is preferably oxygen; and also preferably, sulfur; - R12, R13, R14, R15, R16, R17 and R18 are preferably H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl; or - R12 and R13, together with the atoms to which they are bonded, form a cycle with five or six members; which is saturated, partially unsaturated or aromatic; which may comprise, in addition to carbon atoms, one to four nitrogen atoms, one oxygen atom or one sulfur atom; and which, for its part, can be totally or partially halogenated and/or substituted by one to three C1-C6 alkyl groups; specifically preferably, they are H, C1-C6 alkyl or C1-C6 haloalkyl; or - R12 and R13, together with the atoms to which they are bonded, form a six-membered cycle, which is saturated; especially preferably, they are H, C1-C6 alkyl or C1-C6 haloalkyl; more preferably, H, CH3 or CF3; - R16 and R17 are, more preferably, C1-C6 haloalkyl; - R18 is preferably higher than CH3; - R19, R20, R21, R22, R23 and R24 are preferably hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl; or - R21 and R22, together with the atoms to which they are bonded, form a five- or six-membered cycle; which is saturated, partially unsaturated or aromatic; which may comprise, in addition to carbon atoms, one to four nitrogen atoms, one or two oxygen atoms or one or two sulfur atoms; and which, for its part, may be totally or partially halogenated and/or substituted by one or more C1-C6 alkyl groups; specifically preferably, they are hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; or - R21 and R22, together with the atoms to which they are bonded, form a five- or six-membered cycle; which is saturated; and which, for its part, may be totally or partially halogenated and/or substituted by one or more C1-C6 alkyl groups; especially preferably, they are C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; or - R21 and R22, together with the atoms to which they are bonded, form a six-membered cycle, which is saturated; and more preferably, they are CH3, CF3, CF2H or OCF2H; - R25 is preferably C1-C6 alkyl or C1-C6 haloalkyl; - R26 and R27 are preferably hydrogen, halogen or C1-C6 alkyl; and specifically preferably, C1-C6 alkyl; - R28, R29 and R30 are preferably hydrogen, halogen or C1-C6 alkyl; more preferably, halogen or C1-C6 alkyl; preferably superior, halogen; also preferably higher, C1-C6 alkyl; and also preferably higher, hydrogen; - R31 is preferably C1-C6 alkyl; - R32, R33 and R34 are preferably hydrogen, halogen, C1-C6 alkyl or C1-C6 haloalkyl; and specifically preferably, C1-C6 haloalkyl; - R35 and R36 are preferably hydrogen, amino, C1-C6 alkyl or C1-C6 haloalkyl; and specifically preferably, C1-C6 alkyl; - R37 is preferably Cl or CH3; and specifically preferably, CH3.

[041] Phenyl ethers of formula (I) are also preferred, wherein: - Z is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; also preferably, pyridyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[042] Phenyl ethers of formula (I) are also preferred, wherein: - Z is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, it is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably specifically, phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of F, Cl or CH3; and more preferably, phenyl or pyridyl; each of which is unreplaced.

[043] Phenyl ethers of formula (I) are also preferred, wherein: - Z is phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; specifically preferably, phenyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of F, Cl or CH3; and most preferably, it is unsubstituted phenyl.

[044] Phenyl ethers of formula (I) are also preferred, wherein: Z is pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; specifically preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of F, Cl or CH3; most preferably, it is unsubstituted.

[045] Phenyl ethers of formula (I) are also preferred, in which: Z is selected from the group consisting of Z1 to Z29: where: * indicates the connection point from Z to X; * * indicates the connection point from Z to Q; and * Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H.

[046] Phenyl ethers of formula (I) are also preferred, in which: - Z is selected from the group consisting of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 , Z12, Z13 and Z21 as defined above; preferably specifically, selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21, as defined above; preferably special, selected from the group consisting of Z1, Z4, Z5, Z6 and Z7, as defined above; and most preferably, selected from the group consisting of Z1 and Z7, as defined above.

[047] Phenyl ethers of formula (I) are also preferred, in which: - Z is selected from the group consisting of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 , Z12, Z13 and Z21 as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H; preferably specifically, selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21, as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H; preferably special, selected from the group consisting of Z1, Z4, Z5, Z6 and Z7, as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H; most preferably selected from the group consisting of Z1 and Z7 as defined above, wherein - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, haloalkyl C1-C6, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H.

[048] Phenyl ethers of formula (I) are also preferred, where: - R1 is H or F; and - R2 is F, Cl or CN.

[049] Phenyl ethers of formula (I) are also preferred, where: - R3 is H, C1-C3 alkyl or C1-C3 alkoxy; and - R4 is H.

[050] Phenyl ethers of formula (I) are also preferred, in which: - R5 is OR6, NR6S(O)2R7 or NR6S(O)2NR7R8, in which - R6 is hydrogen, C1-C6 alkyl, C3-alkenyl or C3-C6 cycloalkyl C1-C6 alkyl; and - R7 and R8 are C1-C6 alkyl.

[051] Phenyl ethers of formula (I) are also preferred, where: - n is 1.

[052] The phenyl ethers of formula (I) are also preferred, where: - Q, W and X are O.

[053] Phenyl ethers of formula (I) are also preferred, in which: - R1 is H or halogen; - R2 is halogen or CN; - R3 is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; - R4 is H; - R5 is OR6, SR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; where - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1 alkoxy -C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, haloalkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1C6 alkyl, haloalkenyloxy C3-C6 alkyl, C3 alkenyloxy -C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1- C6, haloalkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, amino, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1- aminoalkyl C6, (C1-C6 alkyl)C1-C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1-C6 aminocarbonylalkyl, (C1-C6 alkyl)C1-C6 aminocarbonylalkyl or di(C1-C6 alkyl)aminocarbonylC1 alkyl -C6; -N=CR9R10; wherein R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3C6 heterocyclyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R11 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R11)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; R7 is C1-C6 alkyl; R8 is H or C1-C6 alkyl; R9 is phenyl or CH3; R10 is phenyl or CH3; R11 is halogen or C1-C6 alkyl; n is 1 or 2; Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; W is O; X is O; Z is Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z21 as defined above, where - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; Particularly preferred are the phenyl ethers of formula (I), wherein: R1 is H or halogen; R2 is halogen or CN; R3 is H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy; R4 is H; R5 is OR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; where R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, C1- alkylcarbonyl C6 C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl or C3-C6 cycloalkyl C1-C6 alkyl; R7 is C1-C6 alkyl; R8 is H or C1-C6 alkyl; - n is 1; - Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; - W is O; - X is O; and - Z is selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21 as defined above, where Ra, Rb, Rc, Rd and Re, independently among themselves, they are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; Particular preference is given to the phenyl ethers of formula (I), wherein: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, C1-C3 alkyl or C1-C3 alkoxy; - R4 is H; - R5 is OR6 or NR6S(O)2R7, where - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl or C1-C6 haloalkyl; and - R7 is C1-C6 alkyl; - n is 1; - Q is O or S; - W is O; - X is O; e - Z is selected from the group consisting of Z1, Z4, Z5, Z6 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1 alkyl -C6, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; more preferably, they are the phenyl ethers of formula (I), where: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, CH3 or OCH3; - R4 is H; - R5 is OR6 or NR6S(O)2R7; where - R6 is hydrogen, C1-C6 alkyl or C3-C6 alkynyl; and - R7 is C1-C6 alkyl; - n is 1; - Q is O; - W is O; - X is O; and - Z is selected from the group consisting of Z1 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy or C1-C6 haloalkoxy.

[054] Phenyl ethers of formula (I) are also preferred, where: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, CH3 or OCH3; - R4 is H; - R5 is OR6, SR6, NR7R8, NR6OR6, NR6S(O)2R7 or NR6S(O)2NR7R8; where - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1 alkoxy -C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, haloalkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1C6 alkyl, haloalkenyloxy C3-C6 alkyl, C3 alkenyloxy -C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl C1- C6, haloalkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, amino, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (alkylcarbonyl or di(C1-C6 alkyl)aminocarbonylC1-C6alkyl; -N=CR9R10, where R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 heterocyclyl, C3-C6 heterocyclyl, C1-C6 alkyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R14 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R9)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; - R7 and R8, independently of each other, are R9 or together they form a carbocycle with 3 to 7 members; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R10)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; - n is 1; - Q is O; - W is O; - X is O; and - Z is selected from the group consisting of Z1 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy or C1-C6 haloalkoxy.

[055] Specific preference is given to phenyl ethers of formula (Ia), corresponding to formula (I) in which Y is Y2, R19 is Br, R20 is CF3, R21 is CH3 and R4 is H, n is 1, Q , W and X are O and Z is Z-1 as defined, where Ra, Rb, Rc and Rd are H: wherein the variables R1, R2, R3 and R5 have the meanings, particularly the preferred meanings, as defined above.

[056] Special preference is given to compounds of formulas Ia1 to Ia36 of Table A, in which the definitions of the variables R1, R2, R3 and R5 are of specific importance for the compounds according to the present invention, not just in combination among themselves, but also separately in each case. TABLE A

[057] Also preferred are the phenyl ethers of formula (Ib), particularly preferred are the phenyl ethers of formulas (Ib1) to (Ib36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y2, where R28 is Cl, R23 is OCHF2 and R24 is CH3:

[058] Also preferred are the phenyl ethers of formula (Ic), particularly preferred are the phenyl ethers of formulas (Ic1) to (Ic36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13 , where A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2- CHF-CH2)-:

[059] Also preferred are the phenyl ethers of formula (Id), particularly preferred are the phenyl ethers of formulas (Id1) to (Id36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13 , in which A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2- CHF-CH2)- in the form of the stereoisomer (6S, 7aR):

[060] Also preferred are the pyridyl ethers of formula (Ie), particularly preferred are the pyridyl ethers of formulas (Ie1) to (Ie36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y68, where A1 is O, R12 is CF3 and R35 is CH3:

[061] Also preferred are the phenyl ethers of formula (If), particularly preferred are the phenyl ethers of formulas (If1) to (If36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where Y is Y20 and A1 is O:

[062] Also preferred are the phenyl ethers of formula (Ig), particularly preferred are the phenyl ethers of formulas (Ig1) to (Ig36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y31 , where A1 and A2 are O and R26 and R27 are CH3:

[063] Also preferred are the phenyl ethers of formula (Ih), particularly preferred are the phenyl ethers of formulas (Ih1) to (Ih36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y37 , where A1 is O, A4 is S and R21 and R22 together form -(CH2)4-:

[064] Also preferred are the phenyl ethers of formula (Ii), particularly preferred are the phenyl ethers of formulas (Ii1) to (Ii36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y38, where A1 is O and R28 is C(CH3)3:

[065] Also preferred are the phenyl ethers of formula (Ik), particularly preferred are the phenyl ethers of formulas (Ik1) to (Ik36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y39, where A1 is S and R21 and R22 together form -(CH2-C(CH3)2- CH2)-:

[066] Also preferred are the phenyl ethers of formula (Il), particularly preferred are the phenyl ethers of formulas (Il1) to (Il36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y42, where R30 is Cl, R14 is H, R16 is CF3 and R15 is H:

[067] Also preferred are the phenyl ethers of formula (Im), particularly preferred are the phenyl ethers of formulas (Im1) to (Im36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y48, where A1 is Cl, R32 is CF3 and R35 is CH3:

[068] Phenyl ethers of formula (In) are preferred, particularly preferred are phenyl ethers of formulas (In1) to (In36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y55 , where A1 is O, R12 is CF3 and R35 and R37 are CH3:

[069] Also preferred are the phenyl ethers of formula (Io), particularly preferred are the phenyl ethers of formulas (Io1) to (Io36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y65, where A1 is O, R12 is H, R13 is CF3 and R35 is CH3:

[070] Phenyl ethers of formula (Ip) are preferred, particularly preferred are phenyl ethers of formulas (Ip1) to (Ip36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y66 , where A1 is O, R12 is CF3 and R13 is H and R35 is CH3:

[071] Also preferred are the phenyl ethers of formula (Iq), particularly preferred are the phenyl ethers of formulas (Iq1) to (Iq36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y67, where A1 and A2 are O, A2 is S, R35 and R36 are CH3:

[072] Phenyl ethers of formula (Ir) are also preferred, particularly preferred are phenyl ethers of formulas (Ir1) to (Ir36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y69 , where A1 and A2 are O and R32 and R33 are H:

[073] Also preferred are the phenyl ethers of formula (Is), particularly preferred are the phenyl ethers of formulas (Is1) to (Is36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Z is Z-7 as defined, where Ra, Rb and Rc are H:

[074] Phenyl ethers of formula (It) are also preferred, particularly preferred are phenyl ethers of formulas (It1) to (It36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y2, where R28 is Cl, R23 is OCHF2 and R24 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[075] Phenyl ethers of formula (Iu) are also preferred, specifically preferably the phenyl ethers of formulas (Iu1) to (Iu36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13, where A1 and A2 are O, R19 is H, R21 and R22 together form -(CH2-CHF- CH2)- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[076] Also preferred are the phenyl ethers of formula (Iv), particularly preferred are the phenyl ethers of formulas (Iv1) to (Iv36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13 , where A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2- CHF-CH2)-, in the form of the stereoisomer (6S, 7aR) and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[077] Also preferred are the pyridyl ethers of formula (Iw), particularly preferred are the pyridyl ethers of formulas (Iw1) to (Iw36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y68, where A1 is O, R12 is CF3, R35 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[078] Also preferred are the phenyl ethers of formula (Ix), particularly preferred are the phenyl ethers of formulas (Ix1) to (Ix36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where A1 is O, R21 and R22 together form -(CH2)4- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[079] Also preferred are the phenyl ethers of formula (Iy), particularly preferred are the phenyl ethers of formulas (Iy1) to (Iy36), which are different from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y31, where A1 and A2 are O, R26 and R27 are CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[080] Phenyl ethers of formula (Iz) are also preferred, specifically preferably the phenyl ethers of formulas (Iz1) to (Iz36), which differ from the corresponding phenyl ethers of formulas (Ia1) to (Ia36) only because Y is Y37, where A1 is O, A4 is S, R21 and R22 together form -(CH2)4- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[081] Phenyl ethers of formula (I.aa) are also preferred, particularly preferred are phenyl ethers of formulas (I.aa.1) to (I.aa.36), which are different from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y38, where A1 is O, R28 is C(CH3)3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[082] Phenyl ethers of formula (I.ab) are also preferred, particularly preferred are phenyl ethers of formulas (I.ab.1) to (I.ab.36), which are different from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y39, where A1 is S and R21 and R22 together form -(CH2- C(CH3)2-CH2)- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[083] Phenyl ethers of formula (I.ac.) are also preferred, particularly preferred are phenyl ethers of formulas (I.ac.1) to (I.ac.36), which are different from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y42, where R30 is Cl, R14 is H, R16 is CF3, R15 is H and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[084] Phenyl ethers of formula (I.ad) are also preferred, particularly preferred are phenyl ethers of formulas (I.ad.1) to (I.ad.36), which are different from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y48, where A1 is O, R32 is CF3, R35 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[085] The phenyl ethers of formula (I.ae) are also preferred, with specific preference being the phenyl ethers of formulas (I.ae.1) to (I.ae.36), which differ from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y55, where A1 is O, R12 is CF3, R35 and R37 are CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[086] The phenyl ethers of formula (I.af) are also preferred, with specific preference being the phenyl ethers of formulas (I.af.1) to (I.af.36), which differ from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y65, where A1 is O, R12 is H, R13 is CF3 and R35 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[087] The phenyl ethers of formula (I.ag.) are also preferred, with specific preference being the phenyl ethers of formulas (I.ag.1) to (I.ag.36), which differ from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y66, where A1 is O, R12 is CF3, R13 is H, R35 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[088] The phenyl ethers of the formula (I.ah.) are also preferred, with specific preference being the phenyl ethers of the formulas (I.ah.1) to (I.ah.36), which differ from the corresponding phenyl ethers of the formulas ( Ia1) to (Ia36) only because Y is Y67, where A1 and A2 are O, A3 is S, R35 and R36 are CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[089] The phenyl ethers of formula (I.ai) are also preferred, with specific preference being the phenyl ethers of formulas (I.ai.1) to (I.ai.36), which differ from the corresponding phenyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y69, where A1 and A2 are O, R32 and R33 are H, and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[090] The phenyl ethers of formula (I) according to the present invention can be prepared by standard organic chemistry processes, for example, by processes A and B below.

[091] Phenyl ethers of formula (I), where Y is a heterocycle, which is linked through an N atom to the central phenyl ring, can be prepared from amino compounds of formula (II) in a manner analogous to known processes:

[092] The methods used to convert compounds (II) into phenyl ethers of formula (I) depend on the nature of the Y group.

[093] These methods are described, elsewhere, in Chemical Biology & Drug Design 2014, 84 (4), 431-442 (Y8, Y9), Bioorganic & Medicinal Chemistry 2010, 18 (22), 7948-7956 (Y10) , JP 01139580 (Y11), EP 1,157,991 (Y12), EP 311,135 (Y13, Y17, Y38, Y39), DE 39 22 107 (Y14, Y31), JP 11292720 (Y15), US 4,670,043 (Y16) , EP 334,055 (Y17, Y38), US 4,213,773 (Y20), EP 75,267 (Y18), EP 863,142 (Y19), WO 96/18618 (Y21), EP 282,303 (Y22), EP 305,923 (Y23), US 6,333,296 (Y24), Bioorganic & Medicinal Chemistry Letters 2010, 20 (5), 1510-1515 (Y25, Y26), WO 2008/011072 (Y30), DE 39 22 107 (Y14, Y31), JP 07304759 (Y32 ), JP 06016664 (Y33), WO 2008/030902 (Y34), EP 683,160 (Y35), US 5,726,126 (Y36), WO 96/02523 (Y37), WO 92/21684 (Y37), EP 334,055 (Y17 , Y20, Y38), WO 93/03043 (Y39, 62), EP 454,444 (Y50), CN 1687061 (Y51), EP 1,095,935 (Y52), EP 985,670 (Y53), J. Chem. Soc., Perkin Trans; 1: Organic and Bio-Organic Chemistry 1993, (6), 731-5 (Y54), EP 869,123 (Y55), WO 2010/100189 (Y56), WO 99/11634 (Y57), WO 86/00072 (Y58) , WO 2012/002096 (Y59), EP 640,600 (Y60, Y67), Zeitschrift für Chemie 1986, 26 (4), 134-136 (Y61), EP 371,240 (Y63, Y64), WO 98/41093 (Y66), WO 10/145992 (Y67), WO 2000/013508 (Y69) and CN 1355164 (Y70).

[094] Phenyl ethers of formula (I), where Y is a heterocycle, which is linked through a C atom to the central phenyl ring, can also be prepared through a cross-coupling reaction of compounds of formula (III ) with compounds of formula (IV) in the presence of a transition metal catalyst in a manner analogous to known processes (e.g. WO 95/22547 (Y2), WO 98/07720 (Y42), WO 02/042275 (Y42), JP 2009137851 (Y45) and WO 17/036266 (Y65):

[095] Among the compounds of formula (III): - M1 is a boronic acid, alkyl ester of boronic acid, Sn-tri(C1-C4 alkyl); especially preferably, B(OH)2, B(O(C1-C10 alkyl))2 or Sn-tri(C1-C4 alkyl); more preferably, BO2C2(CH3)4 (= “B-pin”) or Sn-tri(C1-C4 alkyl).

[096] Among the compounds of formula (VIII): - L1 is a residual group such as halogen or OSO2CF3 (triflate); especially preferably, I, Br, Cl or OSO2CF3; and more preferably, I or Br.

[097] The reaction is normally carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 110 °C, particularly from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and catalyst.

[098] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of compounds of formula (VII) with compounds of formula (VIII) in organic solvent with or without water as co-solvent.

[099] Suitable solvents are those capable of dissolving the compounds of formula (VII) and the compounds of formula (VIII) at least partially and, preferably, completely under the reaction conditions.

[100] Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o, m and p-xylene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF); as well as bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU) , dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP).

[101] Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF) and bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide ( DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). Most preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF). It is also possible to use mixtures of the mentioned solvents.

[102] Examples of suitable metal-containing bases are inorganic compounds that include metal-containing bases, such as alkali metal and alkaline earth metal hydroxides, as well as other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2, Ca(OH)2 and Al(OH)3; oxides of alkali metals and alkaline earth metals, as well as other metal oxides, such as Li2O, Na2O, K2O, MgO and CaO, Fe2O3, Ag2O; alkali metal and alkaline earth metal carbonates, such as Li2CO3, Na2CO3, K2CO3, Cs2CO3, MgCO3 and CaCO3, as well as alkali metal bicarbonates, such as LiHCO3, NaHCO3 and KHCO3; alkali metal and alkaline earth metal phosphates, such as K3PO4 and Ca3(PO4)2; alkali metal and alkaline earth metal acetates, such as sodium acetate or potassium acetate.

[103] Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and Al(OH)3 and alkali metal or alkaline earth metal carbonates such as Li2CO3, Na2CO3, K2CO3, Cs2CO3, MgCO3 and CaCO3 and alkaline earth metal phosphates such as K3PO4; and alkali and alkaline earth metal acetates, such as sodium acetate. Especially preferred bases are inorganic compounds, such as alkali and alkaline earth metal hydroxides, as well as other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and Al(OH)3 and alkaline earth metal phosphates such as K3PO4.

[104] The term base, as used herein, also includes mixtures of two or more, preferably two of the above compounds. Specific preference is given to using a foundation.

[105] The bases are preferably used in 1 to 10 equivalents based on the compound of formula (III), more preferably 1.0 to 5.0 equivalents based on the compound of formula (III), preferably greater than 1 .2 to 2.5 equivalents based on the compound of formula (III).

[106] It may be advantageous to add the offset base over a period of time.

[107] The reaction of compounds of formula (III) with compounds of formula (IV) is conducted in the presence of a catalyst. Examples of suitable catalysts include, for example, palladium-based catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)-palladium(0), bis(triphenylphosphine)palladium(II) chloride or (1,1- bis(diphenylphosphine)-ferrocene)- dichloropalladium (II) and, optionally, appropriate additives such as phosphines such as, for example, P-(o-tolyl)3, triphenylphosphine or BINAP (2,2'-bis(diphenylphosphine)- 1,1'-binaphthyl).

[108] The amount of catalyst is normally 0.01 to 20 mol% (0.0001 to 0.2 equivalents) based on the compounds of formula (III).

[109] The intermediates necessary for the preparation of the phenyl ethers of formula (I) according to the present invention and mentioned in processes A and B above are commercially available or can be prepared by standard organic chemistry processes, e.g. through the following processes.

[110] Amino compounds of formula (II) (required for process A mentioned above) can be prepared by reducing the corresponding nitro compounds (V):

[111] Reduction can be achieved, for example, through treatment with iron powder in acetic acid at temperatures ranging from 0 °C to 100 °C. Alternatively, the reduction can be carried out by means of catalytic hydrogenation in hydrogen gas under pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metallic catalyst such as palladium supported over an inert vehicle such as activated carbon, due to weight of 5 to 20% between metal and vehicle, suspended in a solvent such as ethanol at room temperature (see, for example, WO 2011/137088).

[112] Compounds of formula (III) can be prepared from compounds of formula (VII) in the presence of a transition metal catalyst:

[113] Among the compounds of formula (VII): - L2 is a residual group such as halogen or OSO2CF3 (triflate); especially preferably, I, Br, Cl or OSO2CF3; and more preferably, I or Br.

[114] Compounds of formula (IV) necessary for the preparation of compounds of formula (I) according to process B are commercially available or known from the literature.

[115] Nitro compounds of formula (V) can be prepared by means of a nitration reaction of the corresponding compounds of formula (VI) following known literature procedures (Langlois, B. in Introduction of Nitrogen group by exchange of hydrogen for the nitro group; Baasner, B., Hagemann, H., Tatlow, JC, Eds.; Houben-Weyl, Methods of Organic Chemistry; 1974; 4th Edition, Vol. 11, R-NH2 Compounds, pp. 479870):

[116] Compounds of formula (VI) necessary for the preparation of nitro compounds of formula (V) are commercially available or known from the literature.

[117] Compounds of formula (VII) can be prepared by reacting compounds of formula (VIII) with alkylating agents of formula (IX) in the presence of a base in a manner analogous to known processes (for example, WO 11/137088 ):

[118] Among the alkylating agents of formula (IX): - L3 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, Cl, Br, I, C1-C6 alkyl sulfonate or aryl sulfonate; especially preferably, Cl, Br or I; and more preferably, Cl or Br.

[119] Compounds of formula (VIII) necessary for the preparation of compounds of formula (VII) are commercially available, known in the literature or can be prepared by known methods (for example, WO 11/137088).

[120] Alkylating agents of formula (IX) are commercially available or can be prepared by known methods (e.g., Lowell, Andrew N. et al, Tetrahedron, 6 (30), 5573-5582, 2010; WO 11/ 137088).

[121] To broaden the spectrum of action and achieve synergistic effects, the phenyl ethers of formula (I) can be mixed with a large number of representatives from other groups of herbicidal or growth-regulating active ingredients and then applied simultaneously. Suitable components for mixtures are, for example, herbicides from the classes of acetamides, amides, aryloxyphenoxypropionates, benzofuran, benzoic acids, benzothidiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazoles, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridines inocarboxamides, pyrimidinediones, quinolinecarboxylic acids, semicarbazones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils and ureas.

[122] It may also be beneficial to apply the phenyl ethers of formula (I) alone or in combination with other herbicides, or even in the form of a mixture with other plant protection agents, such as in conjunction with pest control agents, bacteria or phytopathogenic fungi. Also of interest is the miscibility with mineral salt solutions that are used to treat nutritional deficiencies and trace elements. Other additives such as non-phytotoxic oils and oil concentrates can also be added.

[123] In an embodiment of the present invention, the compositions according to the present invention comprise at least one phenyl ether of formula (I) (compound A) and at least one additional active compound selected from herbicides B, preferably herbicides B from class b1 to b15, and security officers C (compound C).

[124] In another embodiment of the present invention, the compositions according to the present invention comprise at least one phenyl ether of formula (I) and at least one additional active compound B (herbicide B).

[125] The additional herbicidal compound B (component B) is preferably selected from herbicides of class b1 to b15: b1. lipid biosynthesis inhibitors; b2. acetolactate synthase inhibitors (ALS inhibitors); b3. photosynthesis inhibitors; b4. protoporphyrinogen-IX oxidase inhibitors: b5. bleaching herbicides; b6. enolpyruvyl synthase shikimate 3-phosphate inhibitors (EPSP inhibitors); b7. glutamine synthetase inhibitors; b8. 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9. mitosis inhibitors; b10. very long chain fatty acid synthesis inhibitors (VLCFA inhibitors); b11. cellulose biosynthesis inhibitors; b12. uncoupling herbicides; b13. auxin herbicides; b14. auxin transport inhibitors; and b15. other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumiluron, dalapon, dazomet, diphenzoquat, diphenzoquat methylsulfate, dimetipin, DSMA, dimron, endotal and its salts, etobenzanid, flamprop, flamprop-isopropyl , flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7 ), methyl azide, methyl bromide, methyl-dimron, methyl iodide, MSMA, oleic acid, oxaziclomephone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (CAS 499223-49-3), its salts and esters; including their agriculturally acceptable salts or derivatives.

[126] Preference is given to compositions according to the present invention that comprise at least one herbicide B selected from herbicides of class b2, b3, b4, b5, b6, b7, b9, b10 and b13.

[127] Specific preference is given to compositions according to the present invention that comprise at least one B herbicide selected from class b4, b6, b7, b9, b10 and b13 herbicides.

[128] Specific preference is given to compositions according to the present invention that comprise at least one B herbicide selected from class b4, b6, b10 and b13 herbicides.

[129] Examples of B herbicides that can be used in combination with the phenyl ethers of formula (I) according to the present invention are: b1. from the group of lipid biosynthesis inhibitors: - ACC herbicides such as aloxidim, aloxidim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxidim, ci-halofop, ci-halofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxidim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuril, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuril, sethoxydim, tepraloxidim, tralkoxidim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H) -one (CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3( 6H)-one (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H) -dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6 -tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- acid methyl ester carbonic tetramethyl-5-oxo-2H-pyran-3-yl (CAS 131233751-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl acid methyl ester carbonic -5-oxo-2H-pyran-3-yl; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- acid methyl ester carbonic tetramethyl-5-oxo-2H-pyran-3-yl (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-acid methyl ester carbonic 5-oxo-2H-pyran-3-yl (CAS 1033760-58-5); and non-ACC herbicides, such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, tiobencarb, thiocarbazil, triallate and vernolate; b2. From the group of als inhibitors:-sulfonylurea, such as amidosulfuron, azimsulfuron, goodsufuron, goodsufuron-methyl, chlorimuron, chlorimuron-methyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, etametsulfuron, etametsulfurron-meethyl, etoxisulfuron, flazassulfuron, flazassulfuron, flazassulfuron Ron, flucetosulfuron, flupirarsulfuron, mulpipripsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron , primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron; - imidazolinones, such as imazametabenzo, imazametabenzo-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr herbicides, triazolopyrimidine, and sulfonanilides, such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florassulam, metosulam, penoxsulam, pyrimisulfan and pyroxs ulam; - pyrimidinyl benzoates, such as bispiribac, bispiribac-sodium, pyribenzoxim, pyriftalid, piriminobac, pyriminobac-methyl, pyritiobac, pyrithiobac-sodium, 1-methylethyl ester of 4-[[[2-[(4,6-dimethoxy-acid) 2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl] acid propyl ester methyl]amino]-benzoic acid (CAS 420138-40-5) and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 4201318-01-8); - sulfonylaminocarbonyltriazolinone herbicides, such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; Among these, a preferred embodiment of the present invention relates to compositions comprising at least one imidazolinone herbicide; b3. from the group of photosynthesis inhibitors: - amicarbazone, photosystem II inhibitors, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1637455-12-9) , 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrole-5-one (CAS 1637453-94-1), 1-(5-tert- butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrole-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrole-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[ 4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2 - one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1- methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3 -methylimidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones, such as ametrin, atrazine, chloridazone, cyanazine, desmethrin, dimetamethrin, hexazinone, metribuzin, prometon, promethrin, propazine, simazine, simetrin, terbumeton, terbuthylazin, terbutrin and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, metabenzotiazuron, methobenzuron, methoxuron, monolinuron, neburon, siduron, tebuthiuron and thidiazuron, phenyl carbamates such as desmedipham, carbutilat, phenmedifam, phenmedifam-ethyl, nitrile herbicides such as bromophenoxim, bromoxynil, their salts and esters, ioxynil, their salts and esters, uracils such as bromacil, lenacil and terbacil, bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil and photosystem I inhibitors such as diquat, diquat dibromide, paraquat, paraquat dichloride and paraquat dimethylsulfate; Among these, a preferred embodiment of the present invention relates to compositions comprising at least one aryl urea herbicide; among these, similarly, a preferred embodiment of the present invention relates to compositions comprising at least one triazine herbicide; among these, similarly, a preferred embodiment of the present invention relates to compositions comprising at least one nitrile herbicide; b4. from the group of protoporphyrinogen IX oxidase inhibitors: - acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzofendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufempir, flufempir-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, flutiacet, flutiacet-methyl, medosafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, tidiazimin, thiafenacil, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]- Ethyl 2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide ( CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 915396-43-9), N- ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro -6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl) -3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6- il)-4,5,6,7-tetrahydroisoindol-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3- oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0) , (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3-methylmethoxybut-2-enoate (CAS 948893-00-3) and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4 - dione (CAS 212754-02-4); b5. from the group of bleaching herbicides: - PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flutamone, norflurazon, picolinafen and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibition , amitrol, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 136113971-0), 2-(2,4-dichlorophenyl)methyl-4 ,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7); b6. from the group of EPSP synthase inhibitors: - glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate); - 7. from the group of glutamine synthase inhibitors: - bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium; b8. from the group of DHP synthase inhibitors: - assulam; b9. from the group of mitosis inhibitors: - compounds of group K1: dinitroanilines, such as benfluralin, butralin, dinitramine, etalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds from the K2 group: carbetamide, chlorprofam, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and profam; among these, compounds of the K1 group, particularly dinitroanilines, are preferred; - 10. from the group of VLCFA inhibitors: - chloroacetamides, such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamid, pretilachlor, propachlor, propisochlor and tenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as difenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and other herbicides such as anilophos compounds, cafenstrol, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9: isoxazoline compounds of formula (I)I are known in the art, for example, from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; Among VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11. from the group of cellulose biosynthesis inhibitors: - chlorthiamid, diclobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b12. from the group of uncoupling herbicides: - dinoseb, dinoterb and DNOC and their salts; - 13. from the group of auxin herbicides: - 2, 4- and its salts and esters, such as claciphos, 2,4-DB and its salts and esters, aminociclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters , dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-methyl, halauxifen and their salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3 ,6) and its salts and esters, triclopyr and its salts and esters, florpirauxifen, florpirauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro- 1H-indol-6-yl)picolinic (CAS 1629965-65-6); b14. from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; and b15. from the group of other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumiluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, diphenzoquat, diphenzoquat methylsulfate, dimetipin, DSMA, dimron, endotal and its salts, etobenzamid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dimron, methyl iodide, MSMA, oleic acid, oxaziclomephone, pelargonic acid, piributicarb, quinoclamine and tridiphane.

[130] Active compounds B and C that contain a carboxyl group can be used in the form of the acid, in the form of an agriculturally useful salt as mentioned above or in the form of an agriculturally acceptable derivative in the compositions according to the present invention.

[131] In the case of dicamba, agriculturally useful salts include those in which the counterion is an agriculturally acceptable cation. Suitable dicamba salts are, for example, dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicambatrolamine, dicamba-N,N -bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butotyl.

[132] Suitable 2,4-D salts are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D- diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammonium, 2,4-D -tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D -lithium and 2,4-D-sodium. Examples of suitable 2,4-D esters are 2,4-D-butyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4 -D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-iso-octyl, 2,4-D-isopropyl, 2,4-D-methyl, 2 ,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and claciphos.

[133] Suitable 2,4-DB salts are, for example, 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammonium. Suitable 2,4-DB esters are, for example, 2,4-DB-butyl and 2,4-DB-iso-octyl.

[134] Suitable dichlorprop salts are, for example, dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable dichlorprop esters are dichlorprop-butotyl and dichlorprop-iso-octyl.

[135] Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-iso- octyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

[136] A suitable MCPB salt is MCPB-sodium. A suitable MCPB ester is MCPB-ethyl.

[137] Suitable clopyralid salts are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium. An example of suitable clopyralid esters is clopyralid-methyl.

[138] Examples of suitable fluroxypyr esters are fluroxypyrmethyl and fluroxypyr-2-butoxy-1-methylethyl, where fluroxypyr-methyl is preferred.

[139] Suitable picloram salts are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable picloram ester is picloram-isoctyl.

[140] A suitable triclopyr salt is triclopyr-triethylammonium. Suitable triclopyr esters are, for example, triclopyrethyl and triclopyrbutoyl.

[141] Suitable chloramben salts and esters include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and 2,3,6-TBA -sodium.

[142] Suitable aminopyralid salts and esters include aminopyralid-potassium, aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxypropyl)ammonium.

[143] Suitable glyphosate salts are, for example, glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium and also the salts of ethanolamine and diethanolamine, preferably glyphosate -diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

[144] Suitable glufosinate salt is, for example, glufosinate-ammonium.

[145] Suitable glufosinate-P salt is, for example, glufosinate-P-ammonium.

[146] Suitable bromoxynyl salts and esters are, for example, bromoxynyl butyrate, bromoxynyl heptanoate, bromoxynyl octanoate, bromoxynyl-potassium and bromoxynyl-sodium.

[147] Suitable ioxonyl salts and esters are, for example, ioxonyl octanoate, ioxonyl-potassium and ioxonyl-sodium.

[148] Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-iso-octyl, mecoprop-methyl, mecoprop-potassium, mecoprop- sodium and mecoproptrolamine.

[149] Suitable mecoprop-P salts are, for example, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P- P-sodium.

[150] Suitable diflufenzopyr salt is, for example, diflufenzopyrsodium.

[151] A suitable naptalam salt is, for example, naptalam sodium.

[152] Suitable aminocyclopyraclor salts and esters are, for example, aminocyclopyraclor-dimethylammonium, aminocyclopyraclor-methyl, aminocyclopyraclor-triisopropanolammonium, aminocyclopyraclor-sodium and aminocyclopyraclor-potassium.

[153] Suitable quinclorac salt is, for example, quinchlorac-dimethylammonium.

[154] Suitable quinmerac salt is, for example, quinmerac-dimethylammonium.

[155] Suitable imazamox salt is, for example, imazamox-ammonium.

[156] Suitable imazapic salts are, for example, imazapic-ammonium and imazapic-isopropylammonium.

[157] Suitable imazapyr salts are, for example, imazapyr-ammonium and imazapyr-isopropylammonium.

[158] A suitable imazaquin salt is, for example, imazaquin-ammonium.

[159] Suitable imazethapyr salts are, for example, imazethapyr-ammonium and imazethapyr-isopropylammonium.

[160] Suitable topramezone salt is, for example, topramezone-sodium.

[161] Particularly preferred B herbicides are B herbicides as defined above; particularly, the herbicides B.1-B.202 listed in Table B. TABLE B

[162] Furthermore, it may be useful to apply the phenyl ethers of formula (I) in combination with safety agents. Safety agents are chemical compounds that prevent or reduce damage to useful plants without causing a greater impact on the herbicidal action of phenyl ethers of formula (I) on unwanted plants. They can be applied before crops (e.g. in seed, sprout or seedling treatments) or in pre-emergence or post-emergence application of the useful plant. The safety agents and phenyl ethers of formula (I) and, optionally, herbicides B can be applied simultaneously or successively.

[163] In another embodiment of the present invention, the compositions according to the present invention comprise at least one phenyl ether of formula (I) and at least one safety agent C (component C).

[164] Suitable safety agents are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids, 1-phenyl- 4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oxyminophenylacetonitrile, acetophenonoximes, 4 ,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5- acids thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarbamates, their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided that they contain an acidic group.

[165] Examples of preferred safety agents C are benoxacor, cloquintocet, ciometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazol, fluxfenim, furilazole, isoxadifen, mefempir, mefenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl )-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836 -31-4), metcamifen (CAS 129531-12-0) and BPCMS.

[166] Particularly preferred security agents C which, as component C, are components of the composition according to the present invention are security agents C as defined above; particularly, the security officers C.1-C.17 listed below in Table C. TABLE C

[167] Active compounds B of groups b1 to b15 and active compounds C are known herbicides and safety agents; see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000, volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS No. 52836-31-4) it is also called R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS No. 71526-07-3) is also called AD-67 and MON 4660.

[168] The assignment of active compounds to corresponding mechanisms of action is based on current knowledge. If several mechanisms of action apply to an active compound, that substance was assigned to only one mechanism of action.

[169] According to a preferred embodiment of the present invention, the composition comprises a herbicide active compound B or component B, at least one, preferably exactly one herbicide B.

[170] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least two, preferably exactly two herbicides B different from each other.

[171] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least three, preferably exactly three different herbicides B.

[172] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least four, preferably exactly four different herbicides B.

[173] According to another preferred embodiment of the present invention, the composition comprises, as security component C or component C, at least one, preferably exactly one security agent C.

[174] According to another preferred embodiment of the present invention, the composition comprises, as component B, at least one, preferably exactly one herbicide B and, as component C, at least one, preferably exactly one safety agent C.

[175] According to another preferred embodiment of the present invention, the composition comprises at least two, preferably exactly two different B herbicides and, as component C, at least one, preferably exactly one C safety agent.

[176] According to another preferred embodiment of the present invention, the composition comprises at least three, preferably exactly three different B herbicides and, as component C, at least one, preferably exactly one C safety agent.

[177] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and, as component B, at least one, preferably exactly one B herbicide.

[178] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and at least two, preferably exactly two different B herbicides.

[179] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and at least three, preferably exactly three different B herbicides.

[180] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and at least four, preferably exactly four different B herbicides.

[181] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and, as a C component, at least one, preferably exactly one security officer C.

[182] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah) and, as component B, at least one, preferably exactly one herbicide B and, as component C, at least one, preferably exactly one safety agent C.

[183] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah), at least two, preferably exactly two different B herbicides and, as C component, at least one, preferably exactly one C safety agent.

[184] According to another preferred embodiment of the present invention, the composition comprises, as component A, at least one, preferably exactly one compound of formula (I), preferably of formula (I.a), (I.b), (I.l), ( I.n), (I.p), (I.q), (I.s), (I.t), (I.ac), (I.ae), (I.ag) or (I.ah), at least three, preferably exactly three different B herbicides and, as C component, at least one, preferably exactly one C safety agent.

[185] According to another preferred embodiment of the present invention, the composition comprises, in addition to a phenyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.b.18), (I.b.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.p.18), (I.p.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.t.18), (I.t.19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I. ag.18), (I.ag.19), (I.ah.18) and (I.ah.19), at least one and especially exactly one compound active as a herbicide of group b4, particularly selected from from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, medosafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1- ethyl methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100) .

[186] According to another preferred embodiment of the present invention, the composition comprises, in addition to a phenyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.b.18), (I.b.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.p.18), (I.p.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.t.18), (I.t.19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I. ag.18), (I.ag.19), (I.ah.18) and (I.ah.19), at least one and especially exactly one herbicide-active compound selected from group b6, particularly selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-trimesium (sulfosate), and glyphosate-potassium.

[187] According to another preferred embodiment of the present invention, the composition comprises, in addition to a phenyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.b.18), (I.b.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.p.18), (I.p.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.t.18), (I.t.19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I. ag.18), (I.ag.19), (I.ah.18) and (I.ah.19), at least one and especially exactly one compound active as a herbicide of group b10, particularly selected from from the group consisting of acetochlor, butachlor, cafenstrol, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazaclor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone. Similarly, preference is given to compositions comprising, in addition to a phenyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.b.18), (I.b. 19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.p.18), (I.p.19), (I.q.18), (I.q.19), (I.s.18), (I.s. 19), (I.t.18), (I.t.19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I.ag. 18), (I.ag.19), (I.ah.18) and (I.ah.19), at least one and especially exactly one herbicide-active compound of group b10, particularly selected from group which consists of isoxazoline compounds of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.

[188] According to another preferred embodiment of the present invention, the composition comprises, in addition to a phenyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.b.18), (I.b.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.p.18), (I.p.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.t.18), (I.t.19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I. ag.18), (I.ag.19), (I.ah.18) and (I.ah.19), at least one and especially exactly one compound active as a herbicide of group b13, particularly selected from from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyraclor, aminocyclopirachlor-potassium, aminocyclopirachlor-methyl, aminopyralid , aminopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium , dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, MCPA, MCPA- 2-ethylhexyl, MCPA-dimethylammonium, quinclorac, quinclorac-dimethylammonium, quinmerac, quinmerac-dimethylammonium, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6 acid -(7-fluoro-1H-indol-6-yl)picolinic acid.

[189] Here and below, the expression “binary compositions” includes compositions comprising one or more, such as 1, 2 or 3 active compounds of formula (I) and one or more, such as 1, 2 or 3 herbicides B or one or more security officers C.

[190] Consequently, the expression “ternary compositions” includes compositions comprising one or more, such as 1, 2 or 3 active compounds of formula (I) and one or more, such as 1, 2 or 3 B herbicides or one or more, such as 1, 2 or 3 security officers C.

[191] In binary compositions comprising at least one compound of Formula (I) as component A and at least one herbicide B, the weight ratio of active compounds A:B is generally in the range of 1:1000 to 1000: 1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:125 to 125:1.

[192] In binary compositions comprising at least one compound of Formula (I) as component A and at least one safety agent C, the weight ratio of active compounds A:C is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:75 to 75:1.

[193] In ternary compositions comprising at least one phenyl ether of formula (I) as component A, at least one herbicide B and at least one safety agent C, the relative parts by weight of components A:B are generally found in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:125 to 125:1 ; the weight ratio of the A:C components is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, of specific preference, in the range of 1:75 to 75:1; and the weight ratio of the B:C components is generally in the range of 1:1000 to 1000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, preferably specific, in the range of 1:75 to 75:1. The weight ratio between components A+B and component C is preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:75. to 75:1.

[194] The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits provided herein, particularly within the preferred limits.

[195] Particularly preferred are the compositions mentioned below which comprise the phenyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1; with special preference, they comprise, as the only compounds active as herbicides, the phenyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1; and preferably higher, which comprise, as the only active compounds, the phenyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1.

[196] Particularly preferred are compositions 1.1 to 1.3653, which comprise phenyl ether (I.a.18) and the substance(s) defined in the corresponding line of Table 1.

TABLE 1

[197] Compositions 1.1 to 1.3653:

[198] Composition 1,200 comprises, for example, phenyl ether I.a.18 and cinmethylin (B.200) (see Table 1, line 1.200; as well as Table B, line B.200).

[199] Composition 2.200 comprises, for example, phenyl ether I.a.19 (see the definition of compositions 2.1 to 2.3653 below) and cinmethylin (B.200) (see Table 1, line 1.200; as well as Table B, line B.200).

[200] Also of special preference are compositions 2.1 to 2.3653 which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.a.19).

[201] Also of special preference are compositions 3.1 to 3.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.b.18).

[202] Also of special preference are compositions 4.1 to 4.3635, which differ from the corresponding compositions 1.1 to 1.3635 only because they comprise, as active compound A, the pyridyl ether of formula (I.b.19).

[203] Also of special preference are compositions 5.1 to 5.3635, which differ from the corresponding compositions 1.1 to 1.3635 only because they comprise, as active compound A, the pyridyl ether of formula (I.l.18).

[204] Also of special preference are compositions 6.1 to 6.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.l.19).

[205] Also of special preference are compositions 7.1 to 7.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.n.18).

[206] Also of special preference are compositions 8.1 to 8.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.n.19).

[207] Also of special preference are compositions 9.1 to 9.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.p.18).

[208] Also of special preference are compositions 10.1 to 10.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.p.19).

[209] Also of special preference are compositions 11.1 to 11.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.q.18).

[210] Also of special preference are compositions 12.1 to 12.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.q.19).

[211] Also of special preference are compositions 13.1 to 13.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.s.18).

[212] Also of special preference are compositions 14.1 to 14.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.s.19).

[213] Also of special preference are compositions 15.1 to 15.3635, which differ from the corresponding compositions 1.1 to 1.3635 only because they comprise, as active compound A, the pyridyl ether of formula (I.t.18).

[214] Also of special preference are compositions 16.1 to 16.3635, which differ from the corresponding compositions 1.1 to 1 only because they comprise, as active compound A, the pyridyl ether of formula (I.t.19).

[215] Also of special preference are compositions 17.1 to 17.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ac.18).

[216] Also of special preference are compositions 18.1 to 18.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ac.19).

[217] Also of special preference are compositions 19.1 to 19.3653 which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ae.18).

[218] Also of special preference are compositions 20.1 to 20.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ae.19).

[219] Also of special preference are compositions 21.1 to 21.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ag.18).

[220] Also of special preference are compositions 22.1 to 22.3653, which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ag.19).

[221] Also of special preference are compositions 23.1 to 23.3653 which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ah.18).

[222] Also of special preference are compositions 24.1 to 24.3653 which differ from the corresponding compositions 1.1 to 1.3653 only because they comprise, as active compound A, the phenyl ether of formula (I.ah.19).

[223] The present invention also relates to agrochemical compositions comprising at least one auxiliary and at least one phenyl ether of formula (I) according to the present invention.

[224] An agrochemical composition comprises a pesticide-effective amount of a phenyl ether of formula (I). The expression "effective amount" indicates an amount of the composition of compounds I, which is sufficient to control unwanted plants, especially for control of unwanted plants in crops (i.e. cultivated plants) and which does not result in substantial damage to the treated plants. This amount can vary over a wide range and depends on several factors, such as the plants to be controlled, the material or producing plants treated, the climatic conditions and the specific phenyl ether of formula (I) used.

[225] The phenyl ethers of formula (I), their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, such as solutions, emulsions, suspensions, dry powders, powders, pastes, granules, presses, capsules and their mixtures. Examples of types of agrochemical compositions are suspensions (e.g. SC, OD and FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES and ME), capsules (e.g. CS and ZC ), pastes, tablets, dry or wettable powders (e.g. WP, SP, WS, DP and DS), pressed (e.g. BR, TB and DT), granules (e.g. WG, SG, GR, FG, GG and MG), insecticidal articles (e.g. LN) and also gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and other types of agrochemical compositions are defined in Catalog of Pesticide Formulation Types and International Coding System, Technical Monograph No. 2, 6th edition, May 2008, CropLife International.

[226] Agrochemical compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation Technology, Wiley VCH, Weinheim, 2001; or Knowles, New Developments in Crop Protection Product Formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[227] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, humectants, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants , compatibilizers, bactericides, antifreeze agents, antifoam agents, dyes, adhesives and binders.

[228] Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions with medium to high boiling points, such as kerosene and diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene and alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol and cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, gammabutyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and dimethylamides of fatty acids; and their mixtures.

[229] Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, lime, limestone, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas; products of vegetable origin, such as cereal dough, tree bark dough, wood dough, nut shell dough and mixtures thereof.

[230] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solubilizers, humectants, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, United States, 2008 (International Edition or North American Edition).

[231] Suitable anionic surfactants are alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, oil and fatty acid sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of oils and fatty acids, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, carboxylated alcohol or alkylphenol ethoxylates.

[232] Suitable non-ionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, esters of glucose and sucrose or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohols or vinyl acetate.

[233] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising blocks of polyethylene oxide and polypropylene oxide or type A-B-C comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

[234] Suitable adjuvants are compounds that have negligible or no pesticidal activity in themselves and that improve the biological performance of the phenyl ethers of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Additional examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[235] Suitable thickeners are polysaccharides (such as xanthan gum and carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[236] Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

[237] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[238] Suitable defoaming agents are silicones, long-chain alcohols and fatty acid salts.

[239] Suitable dyes (for example, in red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic dyes (e.g. iron oxide, titanium oxide and iron hexacyanoferrate) and organic dyes (such as alizarin, azo and phthalocyanine dyes).

[240] Suitable binders or adhesives are polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, synthetic or biological waxes and cellulose ethers.

[241] Examples of types of agrochemical compositions and their preparation are: i. water-soluble concentrates (SL, LS): 10-60% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from of the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention and 5-15% by weight of wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or solvent water-soluble (e.g. alcohols) up to 100% by weight. The active substance dissolves when diluted with water; ii. Dispersible concentrates (DC): 5-25% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the compounds herbicides B (component B) and safety agents C (component C) according to the present invention and 1-10% by weight of dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) until 100% by weight. Dilution with water generates dispersion; iii. Emulsifiable concentrates (EC): 15-70% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the compounds herbicides B (component B) and safety agents C (component C) according to the present invention and 5-10% by weight of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in insoluble organic solvent in water (e.g. aromatic hydrocarbon) up to 100% by weight. Dilution with water generates an emulsion; iv. Emulsions (EW, EO and ES): 5-40% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention and 1-10% by weight of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water up to 100% by weight using an emulsifying machine and transformed into a homogeneous emulsion. Dilution with water generates an emulsion; v. Suspensions (SC, OD and FS): In a stirred ball mill, 20-60% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are fragmented with addition of 2-10% by weight of dispersants and wetting agents (e.g. , sodium lignosulfonate and alcohol ethoxylate), 0.1-2% by weight thickener (e.g. xanthan gum) and water up to 10% by weight to provide a fine active substance suspension. Dilution with water generates stable suspension of the active substance. For FS type composition, up to 40% by weight of binder (e.g. polyvinyl alcohol) is added; saw. Water-dispersible granules and water-soluble granules (WG and SG): 50-80% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are finely ground with addition of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylate) up to 100% by weight and prepared in the form of water-dispersible or water-soluble granules using technical devices (e.g. extrusion, spray tower and fluidized bed). Dilution with water generates a stable solution or dispersion of the active substance; viii. Water-dispersible powders and water-soluble powders (WP, SP, WS): 50-80% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are ground in a rotor-stator with addition of 1-5% by weight of dispersants (for e.g., sodium lignosulfonate), 1-3% by weight of wetting agents (e.g., alcohol ethoxylate) and solid carrier (e.g., silica gel) up to 100% by weight. Dilution with water generates a stable solution or dispersion of the active substance; viii. Gel (GW, GF): In an agitated ball mill, 5-25% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least an additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are fragmented with addition of 3-10% by weight of dispersants (e.g. sodium lignosulfonate) , 1-5% by weight thickener (e.g. carboxymethyl cellulose) and water up to 100% by weight to provide a fine suspension of the active substance. Dilution with water generates stable suspension of the active substance; iv. Microemulsion (ME): 5-20% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are added to 5-30% by weight of organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10- 25% by weight mixture of surfactants (e.g. alcohol ethoxylate and arylphenol ethoxylate) and water up to 100%. This mixture is stirred for one hour to spontaneously produce a thermodynamically stable microemulsion; iv. Microcapsules (CS): An oil phase comprising 5-50% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention, 0-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 % by weight of acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) are dispersed in an aqueous solution of protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of a phenyl ether of formula (I) according to the present invention, 040% by weight of water-insoluble organic solvent (e.g., aromatic hydrocarbon) and a monomer of isocyanate (e.g., diphenylmethene 4,4'-diisocyanate) are dispersed in an aqueous solution of protective colloid (e.g., polyvinyl alcohol). The addition of polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. Monomers represent 1-10% by weight. The weight percentage refers to the total CS composition; ix. Dustable powders (DP, DS): 1-10% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from of the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are finely ground and mixed thoroughly with a solid carrier (e.g., finely divided kaolin) up to 100% by weight; x. Granules (GR, FG): 0.5-30% by weight of phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are finely ground and associated with a solid carrier (for example, silicate) up to 100% by weight. Granulation is achieved through extrusion, spray drying or fluidized bed; xi. Ultra-low volume (UL) liquids: 1-50% by weight phenyl ether of formula (I) or herbicidal composition comprising at least one phenyl ether of formula (I) (component A) and at least one additional compound selected from of the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) up to 100% by weight.

[242] Agrochemical compositions of types (i) to (xi) may optionally comprise additional auxiliaries, such as 0.1-1% by weight of bactericides, 5-15% by weight of antifreeze agents, 0.1-1% by weight by weight of antifoaming agents and 0.1-1% by weight of dyes.

[243] Agrochemical compositions and/or herbicidal compositions generally comprise from 0.01 to 95%, preferably from 0.1 to 90% and, particularly, from 0.5 to 75% by weight of the phenyl ethers of formula (I) . The phenyl ethers of formula (I) are used in purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

[244] Seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water-dispersible powders for spray treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are generally used for the treatment of plant propagation materials, particularly seeds. The agrochemical compositions in question provide, after dilution two to ten times, active substance concentrations of 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in ready-to-use preparations. Application can be carried out before or during sowing.

[245] Methods of applying phenyl ethers of formula (I) or their agrochemical compositions and/or herbicidal compositions to plant propagation material, especially seeds, include methods of application by covering, coating, pelletizing, sprinkling, soaking and in furrows of the propagation material. Preferably, phenyl ethers of formula (I) or their agrochemical compositions and/or herbicidal compositions, respectively, are applied to the plant propagation material by a method that does not induce germination, such as by covering, pelletizing, coating and sprinkling the seeds.

[246] Various types of oils, humectants, adjuvants, fertilizers or additional micronutrients and pesticides (such as herbicides, insecticides, fungicides, growth regulators and safety agents) can be added to the phenyl ethers of formula (I) or to the agrochemical compositions and/or herbicidal compositions comprising them in premix form or, where appropriate, not until immediately before use (tank mix). These agents can be mixed with the agrochemical compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[247] The user applies the phenyl ethers of formula (I) according to the present invention or the agrochemical compositions and/or herbicidal compositions comprising them normally from a pre-dosing device, knapsack sprayer, spray tank, spray plane or irrigation system. Typically, the agrochemical composition is compounded with water, buffer and/or additional auxiliaries to the desired application concentration and the ready-to-use spray liquid or agrochemical composition according to the present invention is thus obtained. Typically, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of usable agricultural area.

[248] According to one embodiment, individual components of the agrochemical composition according to the present invention or partially pre-mixed components, such as components comprising phenyl ethers of formula (I) and optionally active substances of groups B and/or C, may be mixed by the user in a spray tank and additional additives and auxiliaries may be added if appropriate.

[249] In a further embodiment, individual components of the agrochemical composition according to the present invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank and can be aggregated additional auxiliaries, if appropriate.

[250] In a further embodiment, individual components of the agrochemical composition according to the present invention or partially pre-mixed components, such as components comprising phenyl ethers of formula (I) and optionally active substances of groups B and/or C, may be applied together (such as after tank mixing) or consecutively.

[251] The phenyl ethers of formula (I) are suitable as herbicides. They are intrinsically suitable, in the form of a suitably formulated composition (agrochemical composition) or herbicidal composition in combination with at least one additional compound selected from the active compounds such as herbicides B (component B) and safety agents C (component C).

[252] The phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising the phenyl ethers of formula (I) control vegetation over non-producing areas very efficiently, especially at high application rates. They act against broadleaf weeds and grasses in crops such as wheat, rice, corn, soybeans and cotton, without causing significant damage to the producing plants. This effect is mainly observed at low application rates.

[253] The phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them are mainly applied to plants by spraying the leaves. At this point, application can be conducted using, for example, water as a vehicle by means of customary spraying methods, using spray liquid quantities of about 100 to 1000 l/ha (e.g. 300 to 400 l/ha). there is). The phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can also be applied by means of the low volume or ultralow volume method, or in the form of microgranules.

[254] The application of the phenyl ethers of formula (I), agrochemical compositions and/or herbicidal compositions comprising them can be carried out before, during and/or after, preferably during and/or after the emergence of undesirable plants.

[255] The phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can be applied before or after emergence, before planting or together with seeds of producing plants. It is also possible to apply the phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them, by means of application to seeds previously treated with the phenyl ethers of formula (I) or the agrochemical compositions and/or the herbicidal compositions comprising them. If the active ingredients are less tolerated by certain producing plants, application methods may be used in which the herbicidal compositions are sprayed, with the aid of spray equipment, in such a way that, as far as possible, they do not come into contact with the leaves of sensitive producing plants, while the active ingredients reach the leaves of undesirable plants growing beneath them or the bare soil surface (post-dried, deposition).

[256] In a further embodiment, the phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can be applied through seed treatment. Seed treatment essentially comprises all the procedures familiar to those skilled in the art (seed covering, seed coating, seed dusting, seed soaking, seed film coating, multi-layer seed coating, seed encrustation, seed dipping, seeds and seed pelleting) based on the phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions prepared with them. At this point, herbicidal compositions can be applied with or without dilution.

[257] The term “seed” comprises seeds of all types, such as corns, seeds, fruits, tubers, seedlings and similar forms. At present, the term seed preferably describes corns and seeds. The seed used may be the seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained through customary cultivation methods.

[258] When used in plant protection, the quantities of active substances applied, that is, the phenyl ethers of formula (I), component B and, if appropriate, component C without formulation aids, are, depending on the type of desired effect, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.5 kg per ha and particularly from 0.1 to 1 kg per ha.

[259] In another embodiment of the present invention, the application rate of the phenyl ethers of formula (I), component B and, if appropriate, component C is 0.001 to 3 kg/ha, preferably 0.005 to 2.5 kg/ha ha and, specifically, 0.01 to 2 kg/ha of active substance (s.a.).

[260] In another preferred embodiment of the present invention, the application rates of the phenyl ethers of formula (I) according to the present invention (total amount of phenyl ethers of formula (I)) are from 0.1 g/ha to 3,000 g/ha, preferably 1 g/ha to 1,000 g/ha, depending on target control, season, target plants and growth stage.

[261] In another preferred embodiment of the present invention, the application rates of the phenyl ethers of formula (I) are in the range of 0.1 g/ha to 5,000 g/ha and, preferably, in the range of 0.5 g/ha to 2,500 g/ha or from 2.5 g/ha to 2,000 g/ha.

[262] In another preferred embodiment of the present invention, the application rate of the phenyl ethers of formula (I) is 0.1 to 1,000 g/ha, preferably 0.5 to 750 g/ha and, more preferably, from 2.5 to 500 g/ha.

[263] The required application rates of B herbicidal compounds are generally in the range of 0.0005 kg/ha to 2.5 kg/ha, preferably in the range of 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/ha of s.a.

[264] The required application rates of C safety agents are generally in the range of 0.0005 kg/ha to 2.5 kg/ha, preferably in the range of 0.005 kg/ha to 2 kg/ha or 0. 01 kg/ha to 1.5 kg/ha of s.a.

[265] When treating plant propagation materials such as seeds, for example by means of dusting, coating or soaking seeds, amounts of active substance of 0.1 to 1,000 g, preferably 1 to 1,000 g, are generally required. more preferably 1 to 100 g and, more preferably, 5 to 100 g, per 100 kg of plant propagation material (preferably seeds).

[266] In another embodiment of the present invention, to treat seeds, the amounts of active substances applied, that is, the phenyl ethers of formula (I), component B and, if appropriate, component C are generally employed in amounts of 0.001 to 10 kg per 100 kg of seeds.

[267] When used to protect materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. Quantities usually applied to protect materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[268] In the case of herbicidal compositions according to the present invention, it does not matter whether the phenyl ethers of formula (I), component B and/or additional component C are formulated and applied together or separately.

[269] In the case of separate application, the order in which the application takes place is of less importance. It is only necessary that the phenyl ethers of formula (I), component B and/or additional component C are applied within a period of time that allows simultaneous action of the active ingredients on the plants, preferably within a period of, at maximum, 14 days, particularly a maximum of 7 days.

[270] Depending on the application method in question, the phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can be additionally employed on an additional series of producing plants to eliminate undesirable plants. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max , Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea potatoes, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot es culent, Medicago sativa , Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

[271] Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. Napus, Brasica Oleracea, Citrus Limon, Citrus Sinensis, Coffea Arabica (Coffea Canephora, Coffea Liberal), Cynodon Dactylon, Glycine Max, Gossypium hirsutum (Gossypium arboreum, gossypium vitifolium) Rdeum Vulgare, Juglans Regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

[272] Especially preferred crops are cereal crops, corn, soybeans, rice, canola, cotton, potatoes, peanuts, or permanent crops.

[273] The phenyl ethers of formula (I) according to the present invention or the agrochemical compositions and/or herbicidal compositions comprising them can also be used in genetically modified plants. The term “genetically modified plants” should be understood as plants whose genetic material has been modified by the use of recombinant DNA methods to include an inserted sequence of DNA that is not native to the genome of that plant species or to exhibit deletion of DNA that was native to the genome of that species, where the modification(s) cannot be easily obtained through breeding, mutagenesis, or natural recombination alone. Often, a specific genetically modified plant will be one that has obtained its genetic modification(s) by inheritance, through a process of propagation or natural cultivation from an ancestral plant whose genome was directly treated using a recombinant DNA method. Typically, one or more genes have been integrated into the genetic material of genetically modified plants in order to enhance certain properties of the plant. These genetic modifications also include, but are not limited to, targeted post-translational modification of protein(s), oligos or polypeptides, for example, through the inclusion within them of amino acid mutation(s) that allow(s), m) or promote glycosylation or polymer additions such as prenylation, acetylation, farnesylation or attachment of PEG moieties.

[274] Plants that have been modified through breeding, mutagenesis or genetic engineering, for example, that have become tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl 3-phosphate shikimate synthase (EPSP) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen IX oxidase inhibitors; lipid biosynthesis inhibitors, such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynyl herbicides (i.e. bromoxynil or ioxynil) as a result of conventional breeding methods or genetic engineering; Furthermore, plants have become resistant to several classes of herbicides through various genetic modifications, such as resistance to glyphosate and glufosinate or both, glyphosate and a herbicide from another class, such as ALS inhibitors, HPPD inhibitors, herbicides auxin or ACCase inhibitors. These herbicide resistance technologies are, for example, described in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and references mentioned there. Several cultivated plants have become tolerant to herbicides through mutagenesis and conventional breeding methods, such as summer canola Clearfield® (Canola, BASF SE, Germany), which is tolerant to imidazolinones such as imazamox, or sunflower ExpressSun® ( DuPont, United States), which is tolerant to sulfonyl ureas such as tribenuron. Genetic engineering methods have been used to make cultivated plants, such as soybeans, cotton, corn, beets and canola, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are in development or are commercially available under the brand names or RoundupReady® (glyphosate tolerant, Monsanto, United States), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).

[275] Furthermore, plants are also covered which, using recombinant DNA methods, are capable of synthesizing one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly Bacillus thuringiensis, such as delta-endotoxins, for example CryIA( b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; plant insecticidal proteins (VIP), such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from bacteria-colonizing nematodes, such as Protorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins; plant lectins, such as barley or pea lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, papain, cystatin or patatin inhibitors; ribosome deactivating proteins (RIP), such as ricin, corn-RIP, Abrin, lufin, saporin or bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as calcium or sodium channel blockers, juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, these insecticidal toxins or proteins should also be expressly understood to include pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains (see, for example, WO 02/015701). Additional examples of such toxins or genetically modified plants capable of synthesizing such toxins are described, for example, in EP-A 374,753, WO 93/007278, WO 95/34656, EP-A 427,529, EP-A 451,878, WO 03/18810 and WO 03/52073. Methods of producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants impose tolerance on plants producing these proteins to weedy pests of all taxonomic groups of arthropods, especially beetles (coleoptera), two-winged insects (diptera), moths (lepidoptera) and nematodes (Nematoda). . Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the publications mentioned above and some of them are commercially available, such as YieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corn cultivars producing of Cry1Ab and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase (PAT)); NuCOTN® 33B (cotton cultivars producing Cry1Ac toxin), Bollgard® I (cotton cultivars producing Cry1Ac toxin), Bollgard® II (cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT® (VIP toxin-producing cotton cultivars); NewLeaf® (potato cultivars that produce the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn cultivars producing Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, cf. WO 03/018810), MON 863 from Monsanto Europe S. A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S. A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).

[276] In addition, also covered are plants that, using recombinant DNA methods, are capable of synthesizing one or more proteins to increase the resistance or tolerance of these plants to bacterial, viral or fungal pathogens. Examples of such proteins are so-called “pathogenesis-related proteins” (PR proteins; see, for example, EP-A 392,225), plant disease resistance genes (such as potato cultivars that express resistance genes that act against derived Phytophthora infestans from the Mexican wild potato, Solanum bulbocastanum) or T4 lysozyme (such as potato cultivars capable of synthesizing these proteins with greater resistance against bacteria such as Erwinia amylovora). Methods of producing such genetically modified plants are generally known to those skilled in the art and described, for example, in the publications mentioned above.

[277] In addition, plants are also covered that, using recombinant DNA methods, are capable of synthesizing one or more proteins to increase productivity (such as biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity, other environmental factors limiting growth or tolerance to pests and fungal, bacterial or viral pathogens of these plants.

[278] In addition, plants that contain, using recombinant DNA methods, modified amounts of ingredients or novel ingredients specifically to improve human or animal nutrition are also covered, such as oilseed crops that produce long-chain omega-3 fatty acids. health benefits or unsaturated omega-9 fatty acids (such as canola Nexera®, Dow Agro Sciences, Canada).

[279] In addition, plants are also covered which, using recombinant DNA methods, contain modified amounts of ingredients or novel ingredients specifically to increase the production of starting material, such as potatoes which produce greater amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

[280] It was further concluded that the phenyl ethers of formula (I) according to the present invention or the agrochemical compositions and/or herbicidal compositions comprising them are also suitable for defoliation and/or dissection of plant parts, for the which are suitable producing plants such as cotton, potatoes, canola, sunflower, soybeans or field beans, particularly cotton. In this particular, agrochemical compositions and/or herbicidal compositions for dissection and/or defoliation of plants, processes for preparing these agrochemical compositions and/or herbicidal compositions and methods of dissection and/or defoliation of plants using the phenyl ethers of formula (I) were found. ).

[281] As desiccants, the phenyl ethers of Formula (I) are particularly suitable for dissecting the aerial parts of productive plants such as potatoes, canola, sunflower and soybeans, but also cereals. This makes it possible to fully mechanically harvest these important producing plants.

[282] It is also of economic interest to facilitate harvesting, which is made possible by concentrating on a certain period of time the dehiscence or reduction of adhesion to the tree, in citrus fruits, olives and other species and varieties of fruits in pomes, drupes and nuts. The same mechanism, i.e., promotion of the development of abscission tissue between fruit part or leaf part and shoot part of plants is also essential for controlled defoliation of useful plants, particularly cotton.

[283] Furthermore, reducing the time interval in which individual cotton plants mature leads to increased fiber quality after harvest.

[284] It was further concluded that the phenyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising the phenyl ethers of formula (I) also very efficiently control PPO-resistant herbs.

[285] Consequently, the present invention also provides a method of controlling the growth of PPO-resistant herbs, which comprises contacting these herbs, their parts, their propagation material or their habitat with phenyl ethers of formula (I), wherein PPO-resistant herbs are herbs that are resistant to PPO-inhibiting herbicides, except the phenyl ethers of formula (I).

[286] The present invention specifically relates to a method of controlling PPO-resistant herbs in crops, which comprises applying phenyl ethers of formula (I) to producing plants, in which said PPO herbicide-resistant herbs occur or may occur.

[287] As used herein, the expressions “PPO inhibitor”, “PPO inhibitor herbicide”, “herbicide that inhibits PPO”, “protoporphyrinogen IX oxidase inhibitor herbicide”, “herbicide that inhibits protoporphyrinogen IX oxidase”, “ protoporphyrinogene oxidase inhibitor herbicide” and “herbicide that inhibits protoporphyrinogene oxidase” are synonymous and designate a herbicide that inhibits the protoporphyrinogene oxidase enzyme in plants.

[288] As used herein, the expressions “PPO-inhibiting herbicide-resistant herb”, “PPO-inhibiting herbicide-resistant herb”, “PPO-inhibitor-resistant herb”, “PPO-resistant herb”, “PPO-resistant herb the herbicide that inhibits protoporphyrinogen IX oxidase”, “herbicide-resistant herb that inhibits protoporphyrinogen IX oxidase”, “herbicide-resistant herbicide that inhibits protoporphyrinogen oxidase” and “herbicide-resistant herb that inhibits protoporphyrinogen oxidase” are synonyms and designate a plant that, with respect to a treatment with an appropriate or above-appropriate rate of herbicide application that inhibits PPO, has inherited, developed, or acquired the ability to: 1. survive that treatment if it is lethal to wild-type weed (i.e., eradicates it). The); or 2. exhibit significant plant growth or thrive after that treatment if it suppresses growth of the wild-type herb.

[289] Effective weed control is defined as suppression of at least 70% of the weeds or their eradication from producing plants, or plant phototoxicity of at least 70% of the weeds, as determined two weeks after treatment.

[290] PPO-resistant herbs are therefore herbs that are not controlled by the application of PPO inhibitors, except the phenyl ethers of formula (I), while the corresponding sensitive biotype is controlled at that rate of use.

[291] “Uncontrolled” indicates at present that, on visual assessment, weed control (herbicidal effect) is < 70% weed suppression or eradication, as determined within two weeks after treatment; and “controlled” indicates that, on visual assessment, weed control is >90% weed suppression or eradication, as determined within two weeks of treatment.

[292] Preferably, PPO-resistant weeds are weeds that are not controlled (i.e., on visual assessment, weed control is < 70% weed suppression or eradication as determined within two weeks of treatment) by the application of herbicides. PPO inhibitors, except for the phenyl ethers of formula (I).

[293] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by the application of PPO inhibitor herbicides selected from azafenidin.

[294] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from azafenidin, falesafen and lactofen.

[295] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by the application of PPO inhibitor herbicides selected from medosafen and lactofen.

[296] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from acifluorfen, azafenidin, carfentrazone, flumiclorac, flumioxazin, medosafen, lactofen, oxadiazon, oxyfluorfen, pyraflufen and sulfentrazone.

[297] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from acifluorfen, carfentrazone, flumiclorac, flumioxazin, falesafen, lactofen, oxadiafon, oxyfluorfen, pyraflufen and sulfentrazone.

[298] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO-inhibiting herbicides, other than phenyl ethers of formula (I), while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication, as determined in two weeks after treatment), at that usage rate.

[299] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from azafenidin, falesafen, and lactofen while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication as determined within two weeks after treatment), at that usage rate.

[300] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from falesafen and lactofen while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication as determined within two weeks of treatment), at that usage rate.

[301] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from acifluorfen, azafenidin, carfentrazone, flumiclorac, flumioxazin, medosafen, lactofen, oxadiazon, oxyfluorfen, piraflufen and sulfentrazone, while the corresponding sensitive biotype is controlled (i.e., on visual assessment, control of the weeds is >90% weed suppression or eradication, as determined within two weeks of treatment), at that rate of use.

[302] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from acifluorfen, carfentrazone, flumiclorac, flumioxazin, falesafen, lactofen, oxadiazon, oxyfluorfen, pyraflufen and sulfentrazone, while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is > 90% weed suppression or eradication, as determined within two weeks of treatment), at that rate of use.

[303] PPO-resistant herbs are also preferably those classified as being “PPO-resistant” and therefore related to Anonymous: List of herbicide resistant weeds by herbicide mode of action - weeds resistant to PPO-inhibitors (URL: http:/ /www.weedscience.org/summary/MOA.aspx).

[304] Particularly preferred PPO-resistant herbs are selected from the group consisting of Acalypha ssp., Amaranthus ssp., Ambrosia ssp., Avena ssp., Conyza ssp., Descurainia ssp., Euphorbia ssp. and Senecio ssp.; with special preference, Amaranthus ssp., Ambrosia ssp. and Euphorbia ssp.; and, most preferably, Amaranthus ssp. and Ambrosia ssp.

[305] Furthermore, particularly preferred PPO-resistant herbs are selected from the group consisting of: - Asian copperleaf (Acalypha australis), cockscomb (Amaranthus hybridus), Palmer amaranth (Amaranthus palmeri), pigweed ( Amaranthus retroflexus); Descurainia sophia), wild peanut (Euphorbia heterophyla) and dead thistle (Senecio vernalis); with special preference, cockscomb (Amaranthus hybridus), Palmer amaranth (Amaranthus palmeri), pigweed (Amaranthus retroflexus), tall/common pigweed (Amaranthus tuberculatus or Amaranthus rudis), carpenter bean (Ambrosia artemisiifolia) and wild peanut (Euphorbia heterophyla); and more preferably, tall/common pigweed (Amaranthus tuberculatus, Amaranthus rudis or Amaranthus tamariscinus) and carpenterwort (Ambrosia artemisiifolia).

[306] Most PPO-resistant herbs, particularly Amaranthus tuberculatus biotypes, are resistant due to deletion of codons on the nuclear-encoded PPX2L gene encoding the PPO enzyme that has dual targets, mitochondria and chloroplasts. This results in loss of the amino acid glycine at position 210 (see, for example, B. G. Young et al, Characterization of PPO-Inhibitor-Resistant Waterhemp (Amaranthus tuberculatus) Response to Soil-Applied PPO-Inhibiting Herbicides, Weed Science 2015, 63, 511 -521).

[307] The second type of mutation, particularly in a resistant biotype of Ambrosia artemisiifolia, was identified as a mutation that expressed the R98L alteration of the PPX2 enzyme (S. L. Rousonelos, R. M. Lee, M. S. Moreira, M. J. VanGessel and P. J. Tranel, Characterization of a Common Ragweed ( Ambrosia artemisiifolia) Population Resistant to ALS- and PPO-Inhibiting Herbicides, Weed Science 60, 2012, 335-344).

[308] Consequently, PPO-resistant herbs are preferably herbs whose Protox enzyme is resistant to the application of PPO inhibitors due to a mutation expressed as ΔG210 or R98L change of said Protox enzyme or equivalents to PPX2L or PPX2, respectively, particularly expressed as change ΔG210 or R98L of the aforementioned Protox enzyme.

[309] The preparation of the phenyluracils of formula (I) is illustrated by examples; The object of the present invention, however, is not limited to the examples provided.

A. EXAMPLES OF PREPARATIONS EXAMPLE 1

[310] Ethyl 2-[[3-[2-Chloro-5-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-4-fluorophenoxy]-2-pyridyl]oxy]acetate :

[311] Step 1: 3-(2-chloro-4-fluoro-5-iodophenoxy)-2-nitropyridine.

[312] To a solution of 5.5 g (20.4 mmol) of 2-chloro-4-fluoro-5-iodophenol (CAS 148254-33-5) in 40 ml of acetonitrile, 3.4 g ( 24.5 mmol) of potassium carbonate and 3.2 g (22.4 mmol) of 3-fluoro-2-nitropyridine (CAS 54231-35-5) at 0 °C under a nitrogen atmosphere. The mixture was stirred for one hour at 0 °C and then for 14 hours at 80 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 5.1 g (14.1 mmol, 69%) of the desired compound 1 from step 1.

[313] Step 2: 3-(2-chloro-4-fluoro-5-iodophenoxy)pyridin-2-amine.

[314] To a solution of 6.6 g (18.2 mmol) of compound 1 from step 1 in 15 ml of THF at 0 °C, 5.1 g (91 mmol) of iron and 50 ml of NH4Cl were added aqueous in drops. The mixture was stirred for three hours at 0°C, filtered and the filter pad was washed with ethyl acetate. The filtrate was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 1 from step 2 (5.6 g), which was used without further purification in the next step.

[315] Step 3: 3-(2-chloro-4-fluoro-5-iodophenoxy)pyridin-2-ol.

[316] To a solution of 3.1 g (45.0 mmol) of sodium nitrite in 59 ml of water at 0 ° C, 59 ml of hydrogen sulphide was added in drops. A solution of 5.5 g (15.0 mmol) of compound 1 from step 2 in 59 ml of acetic acid was added dropwise. The mixture was stirred for one hour at 0 °C. The mixture was diluted with water, filtered and the filter pad was washed with ethyl acetate. The solvent was removed under reduced pressure to give the desired compound 1 from step 3 (4.9 g), which was used without further purification in the next step.

[317] Step 4: Ethyl 2-[[3-(5-bromo-2,4-dichlorophenoxy)-2-pyridyl]oxy]acetate.

[318] To a solution of 17.5 g (47.9 mmol) of compound 1 of step 3 in 200 ml of 1,2-dichloroethane at 85 ° C, 1.7 ml of boron trifluoride and etherate was added of diethyl drops, followed by a solution of 25 g (192 mmol) of ethyl diazoacetate in 30 ml of 1,2-dichloroethane drops. The mixture was stirred for 12 hours at 85 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide compound 1 of step 4 (16.0 g), which was used without further purification in the next step.

[319] 1H NMR (CDCl3, ppm): 7.94 (d, J=3.76 Hz, 1H); 7.31 (d, J=5.77 Hz, 1H); 7.13-7.24 (m, 2H); 6.93 (dd, J=7.65, 4.89 Hz, 1H); 4.95 (s, 2H); 4.17-4.30 (m, 2H); 1.27 (t, J=7.03 Hz, 3H).

[320] Step 5:

[321] To a solution of 2.0 g (4.4 mmol) of compound 1 of step 4 in 20 ml of 1,4-dioxane at 0 ° C under a nitrogen atmosphere, 3.3 g (13. 3 mmol) of bis(pinacolato)diboron, 26 g (26.6 mmol) of potassium acetate and 0.4 g (0.5 mmol) of 1,1'-bis(diphenylphosphine)ferrocene dichloropalladium (II). The mixture was stirred for 24 hours at 90 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 1.8 g (4.0 mmol, 90%) of the desired compound 1 from step 5.

[322] Step 6: 4-chloro-5-(difluoromethoxy)-3-iodo-1-methylpyrazole.

[323] To a solution of 7.7 g (30.4 mmol) of iodine in 40 ml of acetonitrile, 3.1 g (30.4 mmol) of tert-butyl nitrile were added at 0 ° C under an argon atmosphere . The mixture was stirred for one hour at 0°C and then 4.0 g of 4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-amine (CAS 149978-51-8) was added. at 0°C. The mixture was stirred for two hours at 25 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with aqueous Na2S2O3, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 4.5 g (22.8 mmol, 73%) of the desired compound 1 from step 6.

[324] Step 7: 2-[[3-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-4-fluorophenoxy]-2-pyridyl]ox] ethyl acetate.

[325] To a solution of 1.3 g (4.1 mmol) of compound 1 of step 6 in 20 ml of 1,4-dioxane/acetonitrile/water (3:3:1) at 0 ° C under an atmosphere of nitrogen, 1.8 g (4.0 mmol) of compound 1.5, 1.7 g (12.2 mmol) of potassium carbonate and 0.9 g (1.2 mmol) of 1,1'- bis(diphenylphosphine)-ferrocene dichloropalladium (II). The mixture was stirred for 14 hours at 90 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to give 1.2 g (2.4 mmol, 59%) of the desired compound 1.

[326] 1H NMR (CDCl3, ppm): 7.89 (d, J=4.02 Hz, 1H); 7.33 (d, J=9.03 Hz, 1H); 7.17 (dd, J=13.80, 7.03 Hz, 2H); 6.91 (br s, 1H); 6.88 (dd, J=8.03, 2.76 Hz, 1H); 6.69 (s, 1 H); 6.51 (s, 1H); 4.96 (s, 2H); 4.19 (q, J=7.03 Hz, 2H); 3.81 (s, 3H); 1.22 (t, J=7.03 Hz, 3H).

EXAMPLE 2

[327] 2-[[3-[2,4-dichloro-5-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a] pyridin-2-yl)phenoxy]-2-pyridyl]oxy]ethyl acetate:

[328] Step 1: Ethyl 2-[[3-[5-(2-tert-butoxycarbonyl-hydrazino)-2,4-dichlorophenoxy]-2-pyridyl]oxy]acetate.

[329] To a solution of 3.2 g (7.6 mmol) of ethyl 2-[[3-(5-bromo-2,4-dichlorophenoxy)-2-pyridyl]oxy]acetate (synthesized from 5-bromo-2,4-dichlorophenol (CAS 183803-12-5) analogously to compound 1 of step 4 described above) and 3.0 g (CAS 870-46-2, 22.8 mmol) of hydrazinecarboxylate tert-butyl in 50 ml of 1,4 dioxane, 5.0 g (15.2 mmol) of cesium carbonate, 0.5 g (0.9 mmol) of Xantphos and 0.3 g (0.4 mmol) of tris(dibenzylideneacetone)dipalladium (0). The mixture was stirred under a nitrogen atmosphere for 12 hours at 105 °C. The volatile products were evaporated and the residue was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 1.2 g (2.6 mmol, 34%) of the desired compound 2 from step 1.

[330] 1H NMR (CDCl3, ppm): 7.77 (d, J=7.03 Hz, 1H); 7.15-7.27 (m, 3H); 7.07-7.13 (m, 1H); 6.24 (s, 1H); 5.40 (d, J=8.53 Hz, 1H); 3.70 (s, 3H); 1.34 (s, 9H); 1.29 (t, J=7.21 Hz, 3H).

[331] Step 2: Ethyl 2-[[3-(2,4-dichloro-5-hydrazinophenoxy)-2-pyridyl]oxy]acetate.

[332] To a solution of 1.2 g (2.5 mmol) of compound 1 of step 5 in 50 ml of ethyl acetate, 30 ml of a solution of 1 M hydrochloric acid in ethyl acetate was added in drops. The mixture was stirred for 12 hours at 20 °C. The volatiles were evaporated to provide the desired product 2 from step 1 (0.9 g), which was used without further purification in the next step.

[333] Step 3: Ethyl 2-[[3-[2,4-dichloro-5-[(2Z)-2-(2-piperidylene)hydrazino]phenoxy]-2-pyridyl]oxy]acetate.

[334] To a solution of 0.9 g (2.4 mmol) of compound 2 from step 1 in 5 ml of acetic acid, a solution of 0.6 g (4.8 mmol) of 6-methoxy was added -2,3,4,5-tetrahydropyridine (CAS 5693-62-9) in 5 ml of acetic acid. The mixture was stirred for 16 hours at 25 °C. The volatile products were evaporated and the residue was purified by column chromatography on silica (dichloromethane/methanol) to generate 0.7 g (1.5 mmol, 64%) of the desired compound 2 from step 3.

[335] Step 4: 2-[[3-[2,4-dichloro-5-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3 -a]pyridin-2-yl)phenoxy]-2-pyridyl]oxy]ethyl acetate.

[336] To a solution of 0.65 g (1.43 mmol) of compound 2 from step 3 in 10 ml of dichloromethane, 1 ml (7.1 mmol) of triethylamine, 17.5 mg (0. 14 mmol) of DMAP and a solution of triphosgene (0.65 g, 2.15 mmol) in 5 ml of dichloromethane. The mixture was stirred for two hours at -10 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to give 80 mg (0.68 mmol, 48%) of the desired compound 24.

[337] 1H NMR (CDCl3, ppm): 7.93 (d, J=4.03 Hz, 1H); 7.61 (s, 1H); 7.29 (d, J=4.03 Hz, 1H); 7.00 (s, 1H); 6.91 (t, J=3.80 Hz, 1H); 4.92 (s, 2H); 4.20 (t, 2H); 3.66 (t, J=5.80 Hz, 2H); 2.72 (t, J=6.20 Hz, 2H); 1.87-1.98 (m, 4H); 1.23 (t, 3H).

EXAMPLE 3

[338] 2-[[3-[2-Chloro-4-fluoro-5-[(Z)-(3-oxo-5,6,7,8-tetrahydro-[1,3,4]thiadiazole [3,4-a]pyridazin-1-ylidene)amino]phenoxy]-2-pyridyl]oxy]ethyl acetate.

[339] Step 1: Ethyl 2-[[3-(2-chloro-4-fluorophenoxy)-2-pyridyl]oxy]acetate.

[340] To a solution of 52.0 g (0.21 mol) of compound 3 from step 3 in 400 ml of 1,2-dichloroethane at 85 ° C, 5.2 ml of boron trifluoride and boron etherate were added. diethyl drops, followed by a solution of 84 g (0.74 mol) of ethyl diazoacetate in 400 ml of 1,2-dichloroethane drops. The mixture was stirred for 12 hours at 85 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 46.0 g (0.14 mmol, 66%) of the desired compound 3 from step 1.

[341] 1H NMR (CDCl3, ppm): 7.89 (dd, J=4.89, 1.38 Hz, 1H); 7.22 (dd, J=7.91, 2.64 Hz, 1H); 7.09 (dd, J=7.65, 1.38 Hz, 1H); 6.92-7.02 (m, 2H); 6.88 (dd, J=7.78, 5.02 Hz, 1H); 4.94-5.00 (m, 2H); 4.23 (q, J=7.11 Hz, 2H); 1.27 (t, J=7.15 Hz, 3H).

[342] Step 2: Ethyl 2-[[3-(2-chloro-4-fluoro-5-nitrophenoxy)-2-pyridyl]oxy]acetate.

[343] To a solution of 46.0 g (0.14 mol) of ethyl 2-[[3-(2-chloro-4-fluorophenoxy)-2-pyridyl]oxy]acetate (synthesized from 2- chloro-4-fluorophenol (CAS 1996-41-4) analogously to compound 1 of step 4 described above) in 400 ml of sulfuric acid at -10 °C, 30 ml of a solution of fuming nitric acid and acid were added. sulfuric acid (1:1). The mixture was stirred for two hours at -5 °C. The mixture was poured into ice water, filtered and the filter pad was washed with water. The filter cake was dried to generate 48.0 g of the desired compound 3 from step 2, which was used without further purification in the next step.

[344] 1H NMR (CDCl3, ppm): 8.01-8.07 (m, 1H), 8.11 (s, 1H); 7.54 (d, J=6.62 Hz, 1H); 7.38-7.49 (m, 2H); 7.02 (dd, J=7.72, 5.07 Hz, 1H); 5.31 (s, 1H); 4.90 (s, 1H); 4.19 (q, J=7.06 Hz, 2H); 1.23 (t, J=7.06 Hz, 3H).

[345] 3: Ethyl 2-[[3-(5-amino-2-chloro-4-fluorophenoxy)-2-pyridyl]oxy]acetate.

[346] A solution of 48.0 g (0.13 mol) of compound 3 from step 1 in 500 ml of acetic acid was added to 36.0 g (0.65 mol) of iron at 0 ° C. The mixture was stirred for 12 hours at 25 °C, filtered and the filter pad was washed with ethyl acetate. The filtrate was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 3 from step 3 (30.0 g), which was used without further purification in the next step.

[347] Step 4: Ethyl 2-[[3-(2-chloro-4-fluoro-5-isothiocyanatophenoxy)-2-pyridyl]oxy]acetate.

[348] To a solution of 2.0 g (6.0 mmol) of compound 3 from step 2 in a solution of 30 ml of chloroform and aqueous NaHCO3 (1:1), 1.0 g (8.0 mmol) was added. 8 mmol) of thiophosgene for two hours at 0 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 3 from step 4 (1.5 g), which was used without further purification in the next step.

[349] Step 5: Ethyl 2-[[3-[2-chloro-4-fluoro-5-(hexahydropyridazine-1-carbothioylamino)phenoxy]-2-pyridyl]oxy]acetate.

[350] To a solution of 1.5 g (3.9 mmol) of compound 3 from step 3 in 15 ml of dichloromethane under a nitrogen atmosphere, 1.2 g (11.9 mmol) of triethylamine and a solution of 0.7 g (4.4 mmol) of hexahydropyridazine dihydrochloride (CAS 124072-89-5) in 5 ml of dichloromethane. The mixture was stirred for one hour at 27 °C. Volatiles were removed under vacuum. The residue was triturated with water, filtered and the filter pad was washed with water. The filtrate was extracted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4, filtered and the solvent removed under reduced pressure to give the desired compound 3 from step 5 (1.7 g), which was used without further purification in the next step.

[351] Step 6: 2-[[3-[2-chloro-4-fluoro-5-[(Z)-(3-oxo-5,6,7,8-tetrahydro-[1,3, 4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenoxy]-2-pyridyl]oxy]ethyl acetate.

[352] To a 20% triphosgene solution in toluene at -5 °C, a solution of 2.1 g (4.6 mmol) of compound 3 from step 4 in 20 ml of 1,2-dichloroethane was added. at 0°C. The mixture was stirred for 2 hours at 27 °C. The mixture was diluted with water and extracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide 1.6 g of the desired compound 3 (3.3 mmol, 72%).

[353] 1H NMR (CDCl3, ppm): 7.88 (dd, J=4.96, 1.21 Hz, 1H); 7.24 (d, J=9.48 Hz, 1H); 7.12 (dd, J=7.83, 1.21 Hz, 1H); 6.89 (dd, J=7.83, 4.96 Hz, 1H); 6.62 (d, J=7.50 Hz, 1H); 4.96 (s, 2H); 4.22 (q, J=7.06 Hz, 2H); 3.66-3.81 (m, 4H); 1.77-1.94 (m, 4H); 1.26 (t, J=7.17 Hz, 3H).

EXAMPLE 4

[354] 2-[[3-[5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluoro-2-nitrophenoxy]-2-pyridyl] oxy]ethyl acetate.

[355] Step 1: Ethyl (Z)-3-amino-4,4,4-trifluoro-2-methylbut-2-enoate.

[356] To a solution of 36.8 g (186 mmol) of (CAS 344-00-3) in 75 ml of ethanol and 3.8 ml of water, 42.9 g (186 mmol) of ethanol acetate were added. ammonium. The mixture was stirred for 16 hours at 90 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 4 from step 1 (17.0 g), which was used without further purification in the next step.

[357] 1H NMR (CDCl3, ppm): 6.45 (br s, 2H); 4.14-4.22 (m, 2H); 1.77-1.93 (m, 3H); 1.29 (t, J=7.09 Hz, 3H).

[358] Step 2: 2-(dimethylamino)-5-methyl-4-(trifluoromethyl)-1,3-oxazin-6-one.

[359] To a solution of 23.6 g (120 mmol) of compound 4 from step 1 in 300 ml of chloroform, 19.5 g (120 mmol) of (dicoromethylene)dimethylammonium chloride (CAS 33842-02- 3). The mixture was stirred for 16 hours at 25 °C. The mixture was diluted with water and extracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 20.0 g (90 mmol, 75%) of the desired compound 4 from step 2.

[360] 1H NMR (CDCl3, ppm): 3.18-3.07 (m, 6H); 2.02 (q, J=2.3Hz, 3H).

[361] Step 3: 3-(2,5-difluorophenyl)-5-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione.

[362] To a solution of 19.8 g (153 mmol) of 2,5-difluoroaniline (CAS 367-30-6) in 40 ml of acetic acid, 17.0 g (77.0 mmol) of compound 4 of step 2. The mixture was stirred for 16 hours at 80 °C. The mixture was cooled with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 4 from step 3 (33.0 g), which was used without further purification in the next step.

[363] Step 4: 3-(2,5-difluorophenyl)-1,5-dimethyl-6-(trifluoromethyl)pyrimidine-2,4-dione.

[364] To a solution of 33.0 g (110 mmol) of compound 4 from step 3 in 40 ml of dimethyl formamide, 30.4 g (220 mmol) of potassium carbonate and 30.0 g (211 mmol) were added. ) of methyl iodide. The mixture was stirred for 16 hours at 25 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to generate 13.6 g (42.5 mmol, 39%) of the desired compound 4 from step 4.

[365] 1H NMR (CDCl3, ppm): 7.24-7.12 (m, 2H); 7.00 (ddd, J=3.0, 5.5, 8.1 Hz, 1H); 3.56 (q, J=2.1 Hz, 3H); 2.25 (q, J=4.6 Hz, 3H).

[366] Step 5: 3-(2,5-difluoro-4-nitrophenyl)-1,5-dimethyl-6-(trifluoromethyl)pyrimidine-2,4-dione.

[367] To a solution of 10.7 g (33.4 mol) of compound 4 from step 4 in 40 ml of sulfuric acid, a solution of 3.6 ml of fuming nitric acid in 10.7 ml of sulfuric acid in drops at -5 °C. The mixture was stirred for 1.5 hours at -5 °C. The mixture was diluted with ice water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 4 from step 5 (13.7 g), which was used without further purification in the next step.

[368] Step 6: 2-[[3-[5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluoro-2-nitrophenoxy]-2 -pyridyl]oxy]ethyl acetate.

[369] To a solution of 13.7 g (37.5 mmol) of compound 4 from step 5 in 100 ml of dimethylformamide, 1.3 g (80 mmol) of potassium carbonate and 9.7 g ( 49.0 mmol) of ethyl 2-((3-hydroxypyridin-2-yl)oxy)acetate (CAS 353292-81-6). The mixture was stirred for 16 hours at 25 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to give 5.6 g (10.3 mmol, 28%) of the desired compound 4.

[370] 1H NMR (CDCl3, ppm): 7.98 (d, J=4.9 Hz, 1H); 7.87 (d, J=8.7 Hz, 1H); 7.49 (d, J=7.8 Hz, 1H); 7.10 (d, J=6.0 Hz, 1H); 6.98 (dd, J=5.0, 7.7 Hz, 1H); 4.93-4.84 (m, 2H); 4.13-4.09 (m, 2H); 3.50 (d, J=1.9 Hz, 3H); 2.19 (q, J=4.6 Hz, 3H); 2.09-2.00 (m, 3H).

EXAMPLE 5

[371] 2-[[3-[2-Amino-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluorophenoxy]-2-pyridyl] oxy]ethyl acetate.

[372] To a solution of 5.6 g (10.3 mmol) of compound 4 in 200 ml of ethanol, 10 ml of water, 2.9 g (50 mmol) of iron and 2.7 g (50 mmol) of ammonium chloride. The mixture was stirred for 16 hours at 25 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether/ethyl acetate) to give 4.0 g (7.8 mmol, 76%) of the desired compound 5.

[373] 1H NMR (CDCl3, ppm): 7.81 (d, J=4.8 Hz, 1H); 7.19 (d, J=7.9 Hz, 1H); 6.84 (dd, J=5.0, 7.8 Hz, 1H); 6.76 (d, J=6.8 Hz, 1H); 6.60 (d, J=10.9 Hz, 1H); 4.97 (s, 2H); 4.32-4.26 (m, 2H); 4.29 (q, 2H); 3.51 (d, J=1.9 Hz, 3H); 2,252.18 (m, 3H); 1.25 (d, J=1.4 Hz, 3H).

EXAMPLE 6

[374] 2-[[3-[2-Chloro-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluorophenoxy]-2-pyridyl] oxy]ethyl acetate.

[375] To a solution of 4.0 g (7.8 mmol) of compound 5 in 150 ml of acetonitrile, 1.6 g (15.6 mol) of copper (I) chloride, 2.9 g (25 mmol) of isoamyl nitrite and 2.1 g (15.6 mol) of copper (II) chloride. The mixture was stirred for 1.5 hours at 25 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile/water containing trifluoroacetic acid) to give 2.1 g (4.0 mmol, 51%) of the desired compound 6.

[376] 1H NMR (CDCl3, ppm): 7.91 (dd, J=1.5, 5.0 Hz, 1H); 7.37 (d, J=8.8 Hz, 1H); 7.29 (dd, J=1.5, 7.8 Hz, 1H); 6.96-6.88 (m, 2H); 4.93 (d, J=2.5 Hz, 2H); 4.17 (q, J=7.2 Hz, 2H); 3.55-3.48 (m, 3H); 2.20 (q, J=4.6 Hz, 3H); 1.25 (t, J=7.2 Hz, 3H).

[377] The compounds listed below in Tables 1 to 9 can be prepared in a similar way to the example mentioned above: where R4 is H, R5 is OR6, n is 1, Q, W and X are O and Y is Y20, where A1 is O, Z is Z-1 and Ra, Rb, Rc and Rd are H. TABLE 1 where R4 is H, R5 is OR6, n is 1, Q, W and X are O and Y is Y20, where A1 is O, Z is Z-7 and Ra, Rb and Rc are H. TABLE 2 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y2, where R23 is OCF2H, R24 is CH3, R28 is Cl, Z is Z-7 and Ra, Rb and Rc are H. TABLE 3 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y37, where A1 is O, A4 is S, R12 and R13 together form -(CH2)4-, Z is Z-7 and Ra, Rb and Rc are H. TABLE 4 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y67, where A1 and A2 are O, R35 and R36 are CH3, Z is Z-7 and Ra, Rb and Rc are H. TABLE 5 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y65, where A1 is O, R12 is H, R13 is CF3, R35 is CH3, Z is Z- 7 and Ra, Rb and Rc are H. TABLE 6 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y55, where A1 is O, R12 is CF3, R35 is CH3, Z is Z-1 and Ra, Rb, Rc and Rd are H. TABLE 7 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y66, where A1 is O, R12 is CF3, R35 is CH3, Z is Z-1 and Ra, Rb, Rc and Rd are H. TABLE 8 where R3 and R4 are H, R5 is OR6, n is 1, Q, W and X are O and Y is Y42, where R14 and R15 are H, R16 is CF3, R30 is Cl, Z is Z-7 and Ra, Rb and Rc are H. TABLE 9

B. EXAMPLES OF USE:

[378] The herbicidal activity of phenyl ethers of formula (I) was demonstrated through the following greenhouse experiments.

[379] The cultivation containers used were plastic flower pots containing silty sand with about 3.0% humus as substrate. Seeds from test plants were grown separately for each species.

[380] For pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after cultivation through fine-dispensing nozzles. The containers were gently irrigated to promote germination and growth and then covered with transparent plastic hoods until the plants took root. This coating caused uniform germination of the test plants unless it was prevented by the active ingredients.

[381] For post-emergence treatment, test plants were first grown to a height of 3 to 15 cm, depending on the plant's habits, and only then treated with the active ingredients that had been suspended or emulsified in water. For this purpose, test plants were directly cultivated and grown in the same containers or were first grown separately as seedlings and transplanted into the test containers a few days before treatment.

[382] Depending on the species, plants were maintained at 10-25 °C or 20-35 °C, respectively.

[383] The trial period extended for two to four weeks. During this period, the plants received care and their reaction to individual treatments was evaluated.

[384] Assessment was conducted using a scale from 0 to 100. 100 indicates no emergence of plants or complete destruction of at least the aerial parts and 0 indicates no damage or normal course of growth. Good herbicidal activity is provided at values of at least 70 and very good herbicidal activity is provided at values of at least 85.

[385] The plants used in the greenhouse experiments belonged to the following species:

[386] At an application rate of 16 g/ha, compounds (examples) 1, 2, 4, 7, 8, 10, 11, 12, 15, 16, 17, 18 and 19 applied using the post- emergence demonstrated very good herbicidal activity against AMARE, CHEAL, ECHCG and SETVI.

[387] At an application rate of 16 g/ha, compound (example) 9 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL and ECHCG.

[388] At an application rate of 31 g/ha, compound (example) 13 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL and ECHCG.

TABLE 10

[389] Comparison of the herbicidal activity of Example 16 according to the present invention: and compound a-9 known from WO 02/098227: in post-emergence application, control 21 days after treatment (greenhouse):

[390] The data clearly demonstrate the better herbicidal activity and superior crop compatibility of the compounds of formula (I) according to the present invention over the compounds according to the prior art.

[391] The replacement of hydrogen with a methyl group within the uracil moiety not only generates herbicidal activity, but also much better crop compatibility, as achieved by the compound known through WO 02/098227.

TABLE 11

[392] Comparison of the herbicidal activity of Example 17 according to the present invention: and compound a-9 known from WO 02/098227: in pre-emergence application, control 21 days after treatment (greenhouse):

[393] The data clearly demonstrate superior crop compatibility of the compounds of formula (I) according to the present invention over the compounds according to the prior art.

[394] Replacing the uracil ring with a thiouracil ring generates not only the same herbicidal activity, but also better crop compatibility, as achieved by the compound known through WO 02/098227.

Claims (7)

1. PHENYL ETHERS, characterized by being of formula (I): where the variables have the following meanings: - R1 is halogen; - R2 is halogen; - R3 is H; - R4 is H; - R5 is OR6; where - R6 is hydrogen or C1-C6 alkyl; - n is 1; - Q is O; - W is O; - X is O; - Y is a heterocycle selected from the group consisting of Y20, Y42, Y55, Y65 and Y67: where - A1, A2 and A3 are oxygen or sulfur; - R12, R13, R14, R15 and R16 are hydrogen or C1-C6 haloalkyl; R35 and R36 are C1-C6 alkyl; R37 is C1-C6 alkyl; - Z is Z-1 or Z-7 where - symbolizes the connection point from Z to X; - * symbolizes the connection point from Z to Q; and Ra, Rb, Rc and Rd are hydrogen; including their agriculturally acceptable salts or amides, esters and thioesters, provided that the compounds of formula (I) contain a carboxyl group. 2. PHENYL ETHERS, according to claim 1, characterized in that R1 is F and R2 is F or Cl. 3. PHENYL ETHERS, according to any one of claims 1 to 2, characterized in that Y is selected from the group consisting of Y67. 4. HERBICIDAL COMPOSITION, characterized in that it comprises a herbicidally active amount of at least one phenyl ether of formula (I), as defined in claim 1, and at least one inert solid and/or liquid carrier and, if appropriate, at least one surfactant substance. 5. PROCESS FOR PREPARING ACTIVE COMPOSITIONS such as herbicides, characterized in that it comprises mixing a herbicide-active amount of at least one phenyl ether of formula (I), as defined in claim 1, and at least one solid and/or liquid carrier inert and, if desired, at least one surface-active substance. 6. METHOD FOR CONTROLING UNWANTED VEGETATION, characterized in that it comprises maintaining an active amount as herbicide of at least one phenyl ether of formula (I), as defined in claim 1, in action on plants, their environment or on seeds. 7. USE OF PHENYL ETHERS of formula (I), as defined in claim 1, characterized by being as herbicides.